Name: 13965-03-2|Bis(triphenylphosphine)palladium(II) dichloride|98%
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SKU: A306485
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1
[ 13965-03-2 ]
1,2-bis(diphenylphosphinoethynyl)benzene [ No CAS ]
[ 265114-75-8 ]

Yield	Reaction Conditions	Operation in experiment
		The dppeb ligand was synthesized according to literature procedures, and the Pd(O) compound was prepared from a modified literature preparation. In particular, equivalents of the ligand were added to Pd(PPh3)2Cl2 in benzene. The solution was heated and stirred at 60 C. for about 16 hours in benzene to allow complexation and was then reduced with hydrazine. Crystals of the complex suitable for X-ray diffraction were obtained within 72 hours by slow evaporation from CH2Cl2. The structure of the complex exhibits the typical tetrahedral coordination environment expected for a d10 metal center with four phosphine ligands. The P-Pd-P bond angles nearly match the idealized 109.5 geometry. Of more prominent interest are the unique structural features of the metal-chelated enediyne linkage.

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 3112 - 3117
[2]Patent: US6828439,2004,B1 .Location in patent: Page column 29-30

2
[ 603-35-0 ]
palladium dichloride [ No CAS ]
[ 13965-03-2 ]

Yield	Reaction Conditions	Operation in experiment
50%	With carbon monoxide; In toluene; at 125℃; under 7600.51 Torr; for 4h;	In a reactor, PdCl2 (89 mg, 0.5 mmol) and an excess of triphenylphosphine (0.8 g, 3 mmol) were placed in toluene(10 mL) under a carbon monoxide pressure of 10 atm; the reaction mixture was heated at 125 C. After 4 h, the solution was transferred to a Schlenk tube and the solvent was evaporated at reduced pressure. The obtained yellow solid was thereafter characterized as PdCl2(PPh3)2 [44]. Yield = 50 %. 1H NMR (CDCl3, 300 MHz, ppm): 7.7 and7.4 (series of m); 31P{1H} NMR (CDCl3, 121 MHz, ppm),24.5 (s).
	In tetrahydrofuran;Heating / reflux;	A solution of o-bromobenzonitrile (100 g, 0.55 mol) and dichloro-bis (triphenyl) phosphine palladium (3.849g, 0.0055 mol, 1 mole %) [prepared in situ from palladium chloride (0.972 g, 0.0055 mol) and triphenylphosphine (2.877 g. 0.01 1 mole)] and lithium perchlorate (1.46 <n="11"/>g, 0.014 mol, 2.5 mol%) in tetrahydrofuran (550 ml) was placed in a three-necked round- bottomed flask and heated to reflux under inert atmosphere. p-Tolylmagnesium bromide (139 g, 0.715 mol, 1.3 mole eq.) hi tetrahydrofuran (820 ml) was added slowly over 4 hours while maintaining the temperature 67C to 690C. The reaction mixture was stirred at the same temperature for another 30 minutes. The reaction was monitored by GC. GC analysis of the reaction mixture showed OTBN 91% and 4, 4'-dimethydiphenyl 2.7%. Water (100 ml) was added and THF was distilled off under vacuum. Dichloromethane (300 ml) was added and the organic layer was extracted with 15% HCl (100 ml). Dichloromethane was distilled off and heptane (300 ml) was added, refluxed for 30 minutes, and cooled to 0C-5C. The product was filtered.Yield: 85 g.; GC purity: 98%.
	In dimethyl sulfoxide; at 20 - 145℃; for 0.916667h;	EXAMPLE 2; Step I: Preparation of tazarotene hydrochloride salt; [0029] Into a 2L 4-neck round bottom flask, dimethyl sulfoxide (700 ml), palladium chloride (3.83 g), and triphenyl phosphine (14.06 g) were added under stirring under a nitrogen atmosphere at room temperature and the temperature was slowly raised to about 145C. The solution became clear at a temperature of about 145C after about 10 minutes. Then the solution was slowly cooled to room temperature over about 45 minutes. In a separate 2L 4-neck round bottom flask, ethyl-6-chloro-3-nicotinate (96.40 g), 4,4- dimethy-6-ethynylthiochroman (100 g) obtained in Example 1, cuprous iodide (6.5 g), and triethanolamine (TEA) (165 g) were added at room temperature under a nitrogen atmosphere. The reaction mixture was stirred for about 2 to about 5 minutes and the contents from the other round bottom flask (now containing bis(triphenylphosphine) palladium (II) chloride formed in situ) were added to the reaction mixture. The temperature was slowly raised to a temperature of about 98C and maintained for about three hours. After the reaction was completed as determined by TLC, the reaction mixture was cooled to a temperature of about 20C to form tazarotene. The reaction mixture was then filtered, and the resulting cake was washed with DMSO (20 ml). All the filtrate was combined, and ethyl acetate (1 L) was added to the filtrate. The solution was washed with water (3 x 400 ml). The organic layer was separated, and the ethyl acetate was distilled out completely (KFR < 0.2%) under vacuum. An ethyl acetate HCI solution (1000 ml) was added to the residue within 15 minutes. The reaction mixture was maintained for 2 hours at room temperature to form tazarotene hydrochloride salt. The tazarotene hydrochloride solid was filtered and washed with ethyl acetate (2x150 ml). The solid was dried at room temperature for about 6 hours (to remove excess HCl gas). Tazarotene hydrochloride salt appears as a yellow solid after drying. The solid weighed about 140 g. Yield = 81 %, m. p. 112-114 C, purity 99.6 % (by HPLC). [0030] The IR (KBr) spectrum showed stretching at 2204 cm-1 and 1720 cm-1. The ¹H NMR (CDCl3) showed signals at No. 9.2(s,lH), 8.6(lH,d), 7.8 (d,2H), 7.4(d,lH), 4.4 (q,2H), 3.1(dd,2H), 2.0 (dd,2H), 1.5-1.6 (t,3H), 1.2-1.4 (s,6H). The CI Mass showed M+. m/z 352.

With hydrogenchloride; In methanol; water; acetone; for 1h;Reflux;

General procedure: The heteroleptic Pd(II) complexes were prepared in two steps.In the first step, the Pd(II)-organophosphine complex was preparedby dissolving PdCl2 in methanol, along with 3-4 drops ofconcentrated hydrochloric acid. The desired organophosphinewas dissolved in dry acetone and reacted with PdCl2 solution in2:1 M ratio. The reaction mixture was refluxed for 1 h and the solidproduct was filtered off. In the second step, the dichloromethanesolution of Pd-organophosphine was reacted with dithiocarbamicacid or the potassium salt of the dithiocarbamate ligand in 1:1 Mration under reflux conditions, for 6 h. The resulting golden yellowsolid product was obtained by rotary evaporation. The solid productwas recrystallized in conical flask in 20 mL dichloromethaneand n-hexane in a 4:1 by volume ratio. Golden yellow crystals ofcomplexes 1 and 2 were obtained by slow evaporation at roomtemperature and pressure, while the other complexes did notcrystallize.

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 13941 - 13944,4
[2]Catalysis Letters,2014,vol. 144,p. 1717 - 1727
[3]Journal of Molecular Catalysis A: Chemical,2004,vol. 219,p. 191 - 199
[4]Organometallics,2003,vol. 22,p. 1402 - 1413
[5]European Journal of Inorganic Chemistry,1998,p. 1975 - 1985
[6]Patent: WO2008/87656,2008,A2 .Location in patent: Page/Page column 9-11
[7]Organometallics,2008,vol. 27,p. 967 - 975
[8]Patent: WO2005/123713,2005,A1 .Location in patent: Page/Page column 12
[9]Journal of Organometallic Chemistry,2011,vol. 696,p. 473 - 487
[10]Journal of Organometallic Chemistry,2000,vol. 605,p. 184 - 192
[11]Journal of Organometallic Chemistry,2008,vol. 693,p. 1117 - 1126
[12]Applied Organometallic Chemistry,2013,vol. 27,p. 387 - 395
[13]Chemistry - A European Journal,2013,vol. 19,p. 12336 - 12349
[14]European Journal of Organic Chemistry,2015,vol. 2015,p. 5842 - 5855
[15]Organic Letters,2015,vol. 17,p. 4550 - 4553
[16]Journal of Molecular Structure,2016,vol. 1118,p. 250 - 258
[17]Inorganica Chimica Acta,2016,vol. 447,p. 176 - 182
[18]Polyhedron,2017,vol. 127,p. 25 - 35
[19]Applied Organometallic Chemistry,2017,vol. 31
[20]European Journal of Inorganic Chemistry,2017,vol. 2017,p. 2968 - 2979
[21]Polymer,2017,vol. 123,p. 81 - 86
[22]Organic Letters,2020,vol. 22,p. 956 - 959

3
[ 13965-03-2 ]
[ 35486-42-1 ]
ethyl acetate n-hexane [ No CAS ]
[ 497-19-8 ]
[ 98-80-6 ]
[ 726138-31-4 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; water; toluene;	(1) 3,5-diphenylpyridin-2-amine To a solution of <strong>[35486-42-1]2-amino-3,5-dibromopyridine</strong> (2.0 g) and phenylboronic acid (2.0 g) in methanol (15 mL) were added aqueous sodium carbonate solution (15 g, in water 30 mL), toluene (70 mL) and bis(triphenylphosphine)dichloropalladium (0.28 g), and the mixture was heated under reflux for 3 days under nitrogen atmosphere. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solvent: hexane-ethyl acetate (2:1)] to give 3,5-diphenylpyridin-2-amine (1.4 g) as crystals. 1H-NMR (CDCl3) delta: 4.64 (2H, br s), 7.30-7.58 (10H, m), 7.62 (1H, d, J=2.4Hz), 8.33 (1H, d, J=2.4Hz)

Reference： [1]Patent: EP1845081,2007,A1

4
[ 13965-03-2 ]
[ 7647-15-6 ]
[ 25044-96-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	In dichloromethane; water; at 20℃; for 8h;	PdCl2 (PPh3) 2 (50 mg, 0.071 mmol),NaBr (74 mg, 0.71 mmol),10 mL of dichloromethane,And 10 mL of water were sequentially added to a 50 mL round bottom flask,The reaction was stirred at room temperature for 8 hours and the organic layer was separated,Dried over anhydrous sodium sulfate,Filter concentrate,The crude product was recrystallized from dichloromethane / petroleum ether to give red crystals as PdBr2 (PPh3) 2 complex,Yield: 85%.

Reference： [1]Patent: CN106243151,2016,A .Location in patent: Paragraph 0006
[2]Chemistry Letters,1986,p. 1467 - 1470

5
[ 13965-03-2 ]
[ 14221-01-3 ]

Yield	Reaction Conditions	Operation in experiment
98.48%	With formic acid In tetrahydrofuran at 63 - 100℃; Inert atmosphere;	1.2-1.5; 2; 3.2-3.5; 4-5 in the reactor B, add formic acid and heat it to boiling; blow nitrogen gas into the lower part of the liquid level of the reactor B, the nitrogen gas containing the formic acid vapor is led out above the reactor B, and the temperature of the gas is heated to 100 through the heat exchanger ; in the tower reactor C, add 5L isopropyl ether, heat to the liquid surface temperature (63±3) ; the solution obtained in step 1 is added dropwise from the top of the reactor C, and at the same time bubbling under the liquid surface In step 2, the nitrogen containing formic acid vapor derived from the reactor B; a reflux device is provided above the reactor C, and the exhaust gas that cannot be condensed is discharged; the formic acid contained in the exhaust gas that is discharged is condensed and recovered; when observing more precipitation in the reactor C, open the bottom valve and slowly release the liquid phase 1L in the lower part of the reactor, and the precipitation flows out accordingly; the liquid phase released in step 4 is cooled to below 30°C and then introduced into filter device D, and the product tetrakis(triphenylphosphine)palladium is filtered out, dried and packaged after filtration; the filtrate is recovered and put back into reactor C. It should be noted that steps 4 and 5 were repeated for a total of 3 times when more precipitation appeared in the reactor. 30 minutes after the solution in reactor A was added to reactor C, the heating was stopped, and 0.3 mol of formic acid was consumed in reactor B in total. After the device was cooled to room temperature, the whole solution of reactor C was released in batches, filtered, dried and packaged. Filtration was carried out by vacuum filtration, and drying was carried out by introducing nitrogen gas at 80°C and vacuuming under the filter element for 5 minutes.Finally, the obtained products were combined and weighed to obtain 113.8 g of yellow-green crystals with a yield of 98.48%
84%	With sodium hydroxide; tetrabutylammonium hydrogensulfate; triphenylphosphine In tetrahydrofuran byproducts: NaCl, HCl, (C6H5)3PO; stirred at 25°C for 24 h; aq. layer removed, org. layer evaporated at 40°C in vacuo, residue treated with abs. C2H5OH, stirred at 60°C for 20 min, filtered, kept at -15°C for 30 min, filtered (Ar), washed (cold abs. C2H5OH), dried in vacuo; IR, NMR;
83%	With sodium borohydride; triphenylphosphine In ethanol the soln. was cooled in cold water, ppt. was filtered, washed with water, EtOH, heptane;

With hydrazine Inorg. Synth. 13 (1972) 121;

Reference： [1]Current Patent Assignee: ANHUI ZESHENG TECH - CN114933612, 2022, A Location in patent: Paragraph 0037-0049
[2]Ioele, Marcella; Ortaggi, Giancarlo; Scarsella, Marco; Sleiter, Giancarlo [Polyhedron, 1991, vol. 10, p. 2475 - 2476]
[3]Yamazaki, Shinsaku [Inorganic Chemistry, 1982, vol. 21, # 4, p. 1638 - 1640]
[4]Chaignon, Nicholas M.; Fairlamb, Ian J.S.; Kapdi, Anant R.; Taylor, Richard J.K.; Whitwood, Adrian C. [Journal of Molecular Catalysis A: Chemical, 2004, vol. 219, # 2, p. 191 - 199]

6
[ 15617-18-2 ]
[ 13965-03-2 ]

Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 803
[2]Organometallics,1990,vol. 9,p. 1735 - 1747

7
palladium dichloride [ No CAS ]
[ 13965-03-2 ]

Reference： [1]Organometallics,1990,vol. 9,p. 864 - 865
[2]Organometallics,1992,vol. 11,p. 2212 - 2220
[3]Journal of the Chemical Society. Perkin transactions I,1987,p. 2597 - 2604
[4]Canadian Journal of Chemistry,1991,vol. 69,p. 1117 - 1123
[5]Organometallics,1990,vol. 9,p. 864 - 865
[6]Electrochimica Acta,1988,vol. 33,p. 205 - 212
[7]Journal of the Chemical Society, Dalton Transactions,1982,p. 2093 - 2098

8
[ 7647-01-0 ]
[ 24670-32-4 ]
[ 13965-03-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	In acetonitrile (CO); Pd compd. addn. to solvent with HCl, heating in autoclave (70°C, 2 h); cooling, depressurizing, ppt. filtration, washing, drying; identified byIR;

Reference： [1]Cavinato; Toniolo [Journal of Molecular Catalysis A: Chemical, 1996, vol. 105, # 1-2, p. 9 - 15]

9
[ 603-35-0 ]
[ CAS Unavailable ]
[ 28966-81-6 ]

Yield	Reaction Conditions	Operation in experiment
95%	Stage #1: palladium dichloride With lithium chloride In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: triphenylphosphine In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;	1 (1) Synthesis of catalyst Palladium dichloride (1.77g, 1mmol) was dissolved in tetrahydrofuran (180 mL of), the substitution of argon, followed by addition of LiCl (0.85g, 2mmol), stirred at room temperature for 5 minutes, was added to the mixed solution of triphenylphosphine in (5.24g, 2mmol), again replaced with argon, and reacted at room temperature for 2 hours (Scheme 3.2) in an argon atmosphere. After completion of the reaction, filtered, washed with methyl tert-butyl ether to be a catalyst bis(triphenylphosphine)palladium(II) dichloride(yellow solid, 95% yield).
93%	In acetonitrile all manipulations under Ar atm.; PdCl2 suspended in warm MeCN, soln. of P compd. added to suspension at room temp., stirred for 1 h; ppt. filtered off, washed with MeCN, dried under vac.;
88%	With hydrogenchloride In methanol; water for 4h; Inert atmosphere; Reflux;

	In acetonitrile synthesis according to W.L.Stefen et al. Inorg. Chem. 15 (1976) 2432;
	In acetonitrile addn. of phosphine deriv. to soln. of Pd compd. in CH3CN, mixt. refluxedfor 5-6 h; according to W.L. Steffen, G.J. Palenik, Inorg. Chem., 1976, 15, 2432;
	In acetonitrile	2.1 Materials and techniques Palladium chloride (PdCl2), triphenyl phosphine andimidazolidine-2-thione were procured from AldrichSigma Ltd. Trans-PdCl2(PPh3)2 was prepared by reactinga solution of PdCl2 in acetonitrile with 2 moles ofPPh3, by a method analogous to literature method.20 C,H and N analyses were obtained with a ThermoelectronFLASHEA1112 CHNS analyzer. Infrared spectrawere recorded using KBr pellets in the range 4000-200 cm-1on a Pye-Unicam SP-3-300 spectrophotometer.Melting point was determined with an electricallyheated Gallenkamp apparatus. 1H NMR spectra wererecorded on a JEOL AL-300 FT spectrometer operatingat a frequency of 300 MHz using CDCl3 as the solventwith TMS as the internal standard. 31P NMR spectrawere recorded on a Bruker ACP-300 spectrometer operatingat a frequency of 121.5 MHz with H3PO4 as theexternal standard with δ = 0.
	In N,N-dimethyl-formamide

Reference： [1]Current Patent Assignee: ZHENGZHOU DERUI PHARMACEUTICAL TECH - CN108689815, 2018, A Location in patent: Paragraph 0087-0089
[2]Hahn, F. Ekkehardt; Lügger, Thomas; Beinhoff, Matthias [Zeitschrift fur Naturforschung, B: Chemical Sciences, 2004, vol. 59, # 2, p. 196 - 201]
[3]Thomas, Andy A.; Wang, Hao; Zahrt, Andrew F.; Denmark, Scott E. [Journal of the American Chemical Society, 2017, vol. 139, # 10, p. 3805 - 3821]
[4]Lobana, Tarlok S.; Kumari, Poonam; Butcher, Ray J.; Akitsu, Takashiro; Aritake, Yoshikazu; Perles, Josefina; Fernandez, Francisco J.; Vega, M. Cristina [Journal of Organometallic Chemistry, 2012, vol. 701, p. 17 - 26]
[5]Lobana, Tarlok S.; Kaur, Parminderjit; Hundal, Geeta; Butcher, Ray J.; Castineiras, Alfonso [Zeitschrift fur Anorganische und Allgemeine Chemie, 2008, vol. 634, # 4, p. 747 - 753]
[6]Mehra, Vinny; Bains, Amreen Kaur; Hundal, Geeta; Lobana, Tarlok S [Journal of Chemical Sciences, 2017, vol. 129, # 3, p. 359 - 363]
[7]Santra, Biswajit [Polyhedron, 2019, vol. 173]

10
[ 13965-03-2 ]
[ CAS Unavailable ]
[ 24670-32-4 ]

Yield	Reaction Conditions	Operation in experiment
8%	With triphenylphosphine In water; acetonitrile P-compds. soln. purging with CO, heating in autoclave (70°C, 2 h,CO atm.); cooling, depressurizing, ppt. filtration, washing, drying (vac.);
8%	With hydrogenchloride; triphenylphosphine In acetonitrile P-compds. soln. with HCl purging with CO, heating in autoclave (70°C, 2 h, CO atm.); cooling, depressurizing, ppt. filtration, washing, drying (vac.); identified by IR;

Reference： [1]Cavinato; Toniolo [Journal of Molecular Catalysis A: Chemical, 1996, vol. 105, # 1-2, p. 9 - 15]
[2]Cavinato; Toniolo [Journal of Molecular Catalysis A: Chemical, 1996, vol. 105, # 1-2, p. 9 - 15]

11
[ 6322-49-2 ]
[ 13965-03-2 ]
[ 88325-31-9 ]

Reference： [1]Journal of molecular catalysis,1990,vol. 58,p. 251 - 267

12
[ 13965-03-2 ]
[ 30652-11-0 ]
[ 143-66-8 ]
[ 146489-23-8 ]

Reference： [1]Polyhedron,1992,vol. 11,p. 2997 - 3006

13
[ 13965-03-2 ]
[ 12082-03-0 ]
[ 555-57-7 ]
[ 232921-11-8 ]

Yield	Reaction Conditions	Operation in experiment
71%	With CuI; NEt₃ In tetrahydrofuran refluxing (12 h), pptn. on Et2O addn. (room temp.); filtering, evapn., chromy. (SiO2); elem. anal.;

Reference： [1]Gomes, Elton L. S.; Hörner, Manfredo; Young Jr., Victor G.; Dupont, Jairton; Caliman, Vinicius; Casagrande Jr., Osvaldo L. [Organometallics, 1999, vol. 18, # 19, p. 3898 - 3903]

14
[ 13965-03-2 ]
[ 89-73-6 ]
(salicylhydroxamate-O,O')bis(triphenylphosphine)palladium(II) [ No CAS ]

Reference： [1]Dalton Transactions,2003,p. 2691 - 2697

15
[ 13965-03-2 ]
[ 23039-94-3 ]
[ 31237-95-3 ]

Reference： [1]Inorganica Chimica Acta,1978,vol. 30,p. 215 - 220

16
[ 13965-03-2 ]
[ 5351-90-6 ]
salicylaldiminato(thiosemicarbazone)(triphenylphosphane)palladium(II) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	In ethanol; dichloromethane; at 20℃; for 96h;	0.056 g (0.285 mmol) of [H2-(Sal-tsc)] was dissolved in ethanol (25 cm3) and added to [PdCl2(PPh3)2] (0.200 g; 0.285 mmol) in dichloromethane (25 cm3). The mixture was allowed to stand for four days at room temperature. Orange red crystals obtained were filtered, washed with n-hexane and dried. Yield: 69%. Mp 204 C. Anal. Calcd for C26H22N3OSPPd: C, 55.57; H, 3.94; N, 7.47; S, 5.71. Found: C, 56.01; H, 4.32; N, 7.58; S, 5.64%. FT-IR (cm-1) in KBr: 1595 (nuC=N), 1331 (nuC-O), 748 (nuC=S), 1432, 1091, 695 cm-1 (for PPh3); UV-Vis (CH2Cl2), lambdamax: 260 (10,167) nm(dm3 mol-1 cm-1) (intra-ligand transition); 329 (5,963) nm (dm3 mol-1 cm-1) (LMCT); 402 (4511) nm(dm3 mol-1 cm-1) (forbidden (d?d) transition); 1H NMR (DMSO-d6, ppm): delta 8.2 (d,(J = 11.1 Hz) 1H, CH=N), 7.1-7.8 (m, aromatic), delta 9.1 (s, -HN-C=S), 6.5 and 6.6 (2 br s, -NH2).

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 6742 - 6752
[2]New Journal of Chemistry,2008,vol. 32,p. 105 - 114

17
[ 29968-78-3 ]
[ 3375-31-3 ]
[ 13965-03-2 ]
[ 643734-74-1 ]

Reference： [1]Organometallics,2003,vol. 22,p. 5513 - 5517

18
[ 13965-03-2 ]
[ 105309-59-9 ]
[ 7787-70-4 ]
[ 1066-54-2 ]
[ 177991-00-3 ]

Reference： [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 4734 - 4743

19
[ 13782-33-7 ]
[ 603-35-0 ]
[ 13965-03-2 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: diamminedichloropalladium(II) In acetonitrile for 4h; Heating / reflux; Stage #2: triphenylphosphine In acetonitrile Heating / reflux;	10 Palladium diammine dichloride was suspended in acetonitrile at reflux for 4 hrs. 1 mole equivalent of triphenylphosphine was added and the mixture refluxed for several hours after which a clear solution was observed. A basic gas (believed to be ammonia) was evolved during the reaction. A further mole equivalent of triphenylphosphine was added and a yellow precipitate formed immediately. This was filtered and dried. The bright yellow crystals were air stable and were identified as Pd(PPh3J2CI2 by NMR and infra-red spectroscopy.
	at 140℃; Inert atmosphere;	4-6 Example 1 General procedure: 15.2g (50mmol) of bis(acetylacetonate)palladium and 59.0g (225mmol) of triphenylphosphine were added to a 1L reaction kettle, 600mL of N,N-diethylformamide (DEF) was added under stirring, and the vacuum was applied to a vacuum degree. ≤ - 0.08MPa, then replace the air with nitrogen, repeat three times, heat the reaction system to 140±2 through an oil bath, the raw materials are slowly dissolved, and after all the solids are dissolved, a brown-red translucent solution is obtained, remove the oil bath, and cool down to about At 100° C., 3.1 g (about 50 mmol) of 80% hydrazine hydrate was added under rapid stirring for reduction, and the speed of adding hydrazine hydrate was carefully controlled to prevent a large amount of generated gas from causing spraying. After the reaction was completed, the temperature was lowered in the water bath, and a large number of yellow crystals were precipitated. When the reaction system was cooled below 30 ° C, filtration was started, and pressure filtration was performed under nitrogen protection. ±2°C, vacuum drying for 1.5h under the condition of vacuum degree ≤-0.09MPa, cooled to room temperature, nitrogen-filled and refrigerated and protected from light, 57.2g of tetrakis(triphenylphosphine)palladium(0) bright yellow crystal powder was obtained, the yield was 99.0 %.

Reference： [1]Current Patent Assignee: JOHNSON MATTHEY PLC - WO2007/29031, 2007, A1 Location in patent: Page/Page column 5
[2]Current Patent Assignee: ZHEJIANG YUTONG CATALYTIC NEW MAT - CN114456210, 2022, A Location in patent: Paragraph 0011; 0035; 0041-0045

20
[ 13965-03-2 ]
[ 1066-54-2 ]
[ 556112-20-0 ]

Yield	Reaction Conditions	Operation in experiment
	In diisopropylamine	8 Synthesis of 1,2-dichloro-4-ethynylbenzene 440 Example 8 Synthesis of 1,2-dichloro-4-ethynylbenzene 440 Synthesis of Compound 439. A mixture of 438 (5.03 g, 18.4 mmol), (bistriphenylphosiphino)palladium(II) chloride (0.323 g, 0.461 mmol) and copper(I) iodide (0.088 g, 0.461 mmol) in diisopropylamine (40 mL) was heated to 40° C. and trimethylsilyl acetylene (1.99 g, 20.2 mmol) was added. After stirring at 40° C. for 18 h, the reaction mixture was cooled to room temperature, poured into water (120 mL) and then extracted with methylene chloride (3*40 mL). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated. Purification by flash chromatography (silica, hexanes) afforded 439. Synthesis of Compound 440.

Reference： [1]Current Patent Assignee: RESOLVYX PHARMACEUTICALS, INC. - US2011/190242, 2011, A1

21
[ 13965-03-2 ]
[ 1366132-26-4 ]
[ 1366130-17-7 ]

Yield	Reaction Conditions	Operation in experiment
46%	With potassium phosphate; XPhos;bis(dibenzylideneacetone)-palladium(0); In water; butan-1-ol; at 100℃;Inert atmosphere;	The mixture of 6-chloro-3-(1 ,4-dioxa-8-azaspiro[4.5]dec-8-ylcarbonyl)-2- quinolinamine (70 mg, 0.201 mmol), 2-(methyloxy)-3-(1-pyrrolidinylsulfonyl)-5-(4, 4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridine (74.0 mg, 0.201 mmol), K3P04 (128 mg, 0.604 mmol ), Xphos(19.19 mg, 0.040 mmol) and Pd2(dba)3 (18.43 mg, 0.020 mmol) in 1-Butanol ( 2 ml.) and water (0.5 ml.) was heated under nitrogen atmosphere at 100 C overnight. Cooled down and loaded the reaction solution to a column and purified by column chromatograrhy(silica gel, 10% methanol in Ethyl acetate) to give the desire products (53.6 mg, 46 %). LCMS (ES+) m/z 554; 1 H NMR (400 MHz, CHLOROFORM-d) delta ppm 8.57 (d, J=2.34 Hz, 1 H) 8.48 (d, J=2.54 Hz, 1 H) 7.85 (s, 1 H) 7.76 - 7.81 (m, 2 H) 7.73 (s, 1 H) 5.60 (br. s., 2 H) 4.10 (s, 3 H) 3.97 (s, 4 H) 3.74 (none, 4 H) 3.43 (t, J=6.63 Hz, 4 H) 1 .83 - 1 .91 (m, 4 H) 1.21 (s, 5 H).

Reference： [1]Patent: WO2012/37108,2012,A1 .Location in patent: Page/Page column 272

22
[ 13965-03-2 ]
[ 22180-53-6 ]
[ 67-66-3 ]
[ 1215128-71-4 ]
[ClSi(μ-2-mercapto-1-methylimidazolide)₄PdBr]*8chloroform [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	In chloroform at 20℃; for 2191.5h; Inert atmosphere; Schlenk technique;

Reference： [1]Autschbach, Jochen; Sutter, Kiplangat; Truflandier, Lionel A.; Brendler, Erica; Wagler, Joerg [Chemistry - A European Journal, 2012, vol. 18, # 40, p. 12803 - 12813]

23
[ 13965-03-2 ]
[ 197712-82-6 ]
C₃₇H₂₆Cl₂F₂₆N₂PPd [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%		Under a dry N2 atmosphere, to a stirred solution of the salt (0.45 g, 0.5 mmol) and sodium hydride (0.17 g, 0.75 mmol) in THF (10 ml). The reaction mixture was heated under reflux for 4 h. After cooling to room temperature, the volatiles were removed. The residue was charged with [PdCl2(PPh3)]2 (0.22 g, 0.25 mmol) and toluene (5 ml). The mixture was stirred at 110 C for 4 h under N2, then cooled to room temperature and hexane (10 ml) was added. The resulting precipitate was filtered off and recrystallized from CH2Cl2/Et2O. And the product was obtained as a yellow solid (0.29 g, 48%).

Reference： [1]Journal of Fluorine Chemistry,2012,vol. 144,p. 143 - 146,4

24
[ 13965-03-2 ]
[ 4334-74-1 ]
[ 1400568-00-4 ]

Yield	Reaction Conditions	Operation in experiment
55%	With triethylamine; In ethanol; for 6h;Heating; Reflux;	General procedure: 4-Methoxybenzaldehyde thiosemicarbazone (27 mg, 0.13 mmol) was dissolved in ethanol (40 mL) and to this solution was added triethylamine (13 mg, 0.13 mmol) followed by [Pt(PPh3)2Cl2] (100 mg, 0.13 mmol). The mixture was then heated to reflux for 6 h to yield a reddish-orange solution. Evaporation of this solution gave a reddish-orange solid, which was subjected to purification by thin layer chromatography on a silica plate. With benzene-acetonitrile (10:1) as the eluant (CAUTION. Benzene is carcinogenic.) an orange band separated, which was extracted with acetonitrile and evaporation of this extract gave [Pt(PPh3)(L-OCH3)] as an orange crystalline solid. Yield: 55%. Anal. Calc. for C27H24N3OPSPt: C, 48.79; H, 3.61; N, 6.33. Found: C, 48.71; H, 3.62; N, 6.34%. 1H NMR (300 MHz; CDCl3) delta (ppm) (J (Hz)): 3.08 (OCH3); 4.98 (NH2); 5.91 (s, 1H), 6.33 (d, 1H, J = 9.9), 7.00 (d, 1H, J = 8.2), 7.41-7.78 (azomethine + PPh3). IR (cm-1): 1622, 1598, 1579, 1553, 1501, 1462, 1453, 1431, 1217, 1181, 1133, 752, 695, 515.

Reference： [1]Polyhedron,2012,vol. 45,p. 177 - 184,8

25
[ 13965-03-2 ]
[ 5706-83-2 ]
[ 1383954-66-2 ]

Yield	Reaction Conditions	Operation in experiment
59%	With triethylamine; In ethanol; for 6h;Heating; Reflux;	General procedure: 4-Methoxybenzaldehyde thiosemicarbazone (27 mg, 0.13 mmol) was dissolved in ethanol (40 mL) and to this solution was added triethylamine (13 mg, 0.13 mmol) followed by [Pt(PPh3)2Cl2] (100 mg, 0.13 mmol). The mixture was then heated to reflux for 6 h to yield a reddish-orange solution. Evaporation of this solution gave a reddish-orange solid, which was subjected to purification by thin layer chromatography on a silica plate. With benzene-acetonitrile (10:1) as the eluant (CAUTION. Benzene is carcinogenic.) an orange band separated, which was extracted with acetonitrile and evaporation of this extract gave [Pt(PPh3)(L-OCH3)] as an orange crystalline solid. Yield: 55%. Anal. Calc. for C27H24N3OPSPt: C, 48.79; H, 3.61; N, 6.33. Found: C, 48.71; H, 3.62; N, 6.34%. 1H NMR (300 MHz; CDCl3) delta (ppm) (J (Hz)): 3.08 (OCH3); 4.98 (NH2); 5.91 (s, 1H), 6.33 (d, 1H, J = 9.9), 7.00 (d, 1H, J = 8.2), 7.41-7.78 (azomethine + PPh3). IR (cm-1): 1622, 1598, 1579, 1553, 1501, 1462, 1453, 1431, 1217, 1181, 1133, 752, 695, 515.

Reference： [1]Polyhedron,2012,vol. 45,p. 177 - 184,8

26
[ 13965-03-2 ]
[ 1627-73-2 ]
[ 1400568-02-6 ]

Yield	Reaction Conditions	Operation in experiment
63%	With triethylamine; In ethanol; for 6h;Heating; Reflux;	General procedure: 4-Methoxybenzaldehyde thiosemicarbazone (27 mg, 0.13 mmol) was dissolved in ethanol (40 mL) and to this solution was added triethylamine (13 mg, 0.13 mmol) followed by [Pt(PPh3)2Cl2] (100 mg, 0.13 mmol). The mixture was then heated to reflux for 6 h to yield a reddish-orange solution. Evaporation of this solution gave a reddish-orange solid, which was subjected to purification by thin layer chromatography on a silica plate. With benzene-acetonitrile (10:1) as the eluant (CAUTION. Benzene is carcinogenic.) an orange band separated, which was extracted with acetonitrile and evaporation of this extract gave [Pt(PPh3)(L-OCH3)] as an orange crystalline solid. Yield: 55%. Anal. Calc. for C27H24N3OPSPt: C, 48.79; H, 3.61; N, 6.33. Found: C, 48.71; H, 3.62; N, 6.34%. 1H NMR (300 MHz; CDCl3) delta (ppm) (J (Hz)): 3.08 (OCH3); 4.98 (NH2); 5.91 (s, 1H), 6.33 (d, 1H, J = 9.9), 7.00 (d, 1H, J = 8.2), 7.41-7.78 (azomethine + PPh3). IR (cm-1): 1622, 1598, 1579, 1553, 1501, 1462, 1453, 1431, 1217, 1181, 1133, 752, 695, 515.

Reference： [1]Polyhedron,2012,vol. 45,p. 177 - 184,8

27
[ 13965-03-2 ]
[ 5706-80-9 ]
[ 1400568-03-7 ]

Yield	Reaction Conditions	Operation in experiment
57%	With triethylamine; In ethanol; for 6h;Heating; Reflux;	General procedure: 4-Methoxybenzaldehyde thiosemicarbazone (27 mg, 0.13 mmol) was dissolved in ethanol (40 mL) and to this solution was added triethylamine (13 mg, 0.13 mmol) followed by [Pt(PPh3)2Cl2] (100 mg, 0.13 mmol). The mixture was then heated to reflux for 6 h to yield a reddish-orange solution. Evaporation of this solution gave a reddish-orange solid, which was subjected to purification by thin layer chromatography on a silica plate. With benzene-acetonitrile (10:1) as the eluant (CAUTION. Benzene is carcinogenic.) an orange band separated, which was extracted with acetonitrile and evaporation of this extract gave [Pt(PPh3)(L-OCH3)] as an orange crystalline solid. Yield: 55%. Anal. Calc. for C27H24N3OPSPt: C, 48.79; H, 3.61; N, 6.33. Found: C, 48.71; H, 3.62; N, 6.34%. 1H NMR (300 MHz; CDCl3) delta (ppm) (J (Hz)): 3.08 (OCH3); 4.98 (NH2); 5.91 (s, 1H), 6.33 (d, 1H, J = 9.9), 7.00 (d, 1H, J = 8.2), 7.41-7.78 (azomethine + PPh3). IR (cm-1): 1622, 1598, 1579, 1553, 1501, 1462, 1453, 1431, 1217, 1181, 1133, 752, 695, 515.

Reference： [1]Polyhedron,2012,vol. 45,p. 177 - 184,8

28
[ 13965-03-2 ]
[ 5470-48-4 ]
[ 1400568-05-9 ]

Yield	Reaction Conditions	Operation in experiment
62%	With triethylamine; In ethanol; for 6h;Heating; Reflux;	General procedure: 4-Methoxybenzaldehyde thiosemicarbazone (27 mg, 0.13 mmol) was dissolved in ethanol (40 mL) and to this solution was added triethylamine (13 mg, 0.13 mmol) followed by [Pt(PPh3)2Cl2] (100 mg, 0.13 mmol). The mixture was then heated to reflux for 6 h to yield a reddish-orange solution. Evaporation of this solution gave a reddish-orange solid, which was subjected to purification by thin layer chromatography on a silica plate. With benzene-acetonitrile (10:1) as the eluant (CAUTION. Benzene is carcinogenic.) an orange band separated, which was extracted with acetonitrile and evaporation of this extract gave [Pt(PPh3)(L-OCH3)] as an orange crystalline solid. Yield: 55%. Anal. Calc. for C27H24N3OPSPt: C, 48.79; H, 3.61; N, 6.33. Found: C, 48.71; H, 3.62; N, 6.34%. 1H NMR (300 MHz; CDCl3) delta (ppm) (J (Hz)): 3.08 (OCH3); 4.98 (NH2); 5.91 (s, 1H), 6.33 (d, 1H, J = 9.9), 7.00 (d, 1H, J = 8.2), 7.41-7.78 (azomethine + PPh3). IR (cm-1): 1622, 1598, 1579, 1553, 1501, 1462, 1453, 1431, 1217, 1181, 1133, 752, 695, 515.

Reference： [1]Polyhedron,2012,vol. 45,p. 177 - 184,8

29
[ 13965-03-2 ]
[ 292638-85-8 ]
[ 103-26-4 ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium acetate; silver trifluoroacetate; In acetonitrile; at 60℃; for 24h;Schlenk technique; Inert atmosphere;	General procedure: Under N2 atmosphere, NaOAc (4.0 equiv), PPh3 1a (0.5 mmol), PdCl2 (10.0 mol %), AgOOCCF3 (5.0 equiv), CH3CN (2.0 mL) and methyl acrylate 2a (0.6 mmol) were successively added into a Schlenk reaction tube. Then the mixture was stirred at 60 C for 24 h. After cooling to room temperature, the solvent was evaporated in vacuo and then purified by flash column chromatography on silica gel to give the pure product 3a.

Reference： [1]Tetrahedron,2013,vol. 69,p. 2102 - 2106

30
[ 13965-03-2 ]
[ 7341-60-8 ]
C₃₂H₂₆N₃PPdS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With triethylamine; In ethanol; for 5h;Reflux;	To a solution of benzophenone thiosemicarbazone (36 mg, 0.15 mmol) in hot ethanol (30 mL), triethylamine (14 mg, 0.14 mmol) was added followed by Pd(PPh3)2Cl2 (100 mg, 0.14 mmol). The mixture was heated at reflux for 5 h to yield an orange solution. Evaporation of this solution gave an orangish-yellow solid, which was subjected to purification by thin layer chromatography on a silica plate. With benzene as the eluant, a yellow band separated, which was extracted with acetonitrile. Upon evaporation of the acetonitrile extract complex 2 was obtained as a crystalline yellow solid. Yield (56 mg): 63%. Anal. Calcd. for C32H26N3PSPd: C, 61.79; H, 4.19; N, 6.76. Found: C, 61.90; H, 4.30; N, 6.65. 1H NMR (CDCl3, ppm): 4.79 (s, NH2, 2H), 7.39-7.76 (PPh3), 6.73 (t, J = 7.2 Hz, 1H), 6.48 (t, J = 7.5 Hz, 1H), 6.65 (d, J = 7.5 Hz, 1H), 6.34 (d, J = 7.5 Hz, 1H). IR (KBr): 1618, 1568, 1480, 1435, 1314, 1190, 1096, 747, 695 and 531 cm-1.

Reference： [1]Journal of Organometallic Chemistry,2013,vol. 724,p. 281 - 288

31
[ 13965-03-2 ]
[ 2302-93-4 ]
C₂₇H₂₄N₃PPdS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With triethylamine; In ethanol; for 5h;Reflux;	This complex was synthesized by following the same above procedure for complex 2, using acetophenone thiosemicarbazone instead of benzophenone thiosemicarbazone. Yield (53 mg): 67%. Anal. Calcd. for C27H24N3PSPd: C, 57.92; H, 4.29; N, 7.51. Found: C, 57.84; H. 4.37; N, 7.62%. 1H NMR (CDCl3, ppm): 2.35 (s, CH3, 3H), 4.85 (s, NH2, 2H), 7.36-7.68 (PPh3), 7.07 (d, J = 7.5 Hz, 1H), 6.86 (t, J = 7.2 Hz, 1H), 6.49 (t, J = 7.5 Hz, 1H), 6.31 (d, J = 7.5 Hz, 1H). IR (KBr): 1594, 1530, 1480, 1434, 1309, 1096, 745, 692 and 533 cm-1.

Reference： [1]Journal of Organometallic Chemistry,2013,vol. 724,p. 281 - 288

32
[ 13965-03-2 ]
[ 7410-40-4 ]
Pd(Nap-tsc)(PPh3) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	In ethanol; dichloromethane; at 20℃; for 96h;	General procedure: 0.056 g (0.285 mmol) of [H2-(Sal-tsc)] was dissolved in ethanol (25 cm3) and added to [PdCl2(PPh3)2] (0.200 g; 0.285 mmol) in dichloromethane (25 cm3). The mixture was allowed to stand for four days at room temperature. Orange red crystals obtained were filtered, washed with n-hexane and dried. Yield: 69%.

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 6742 - 6752

33
[ 13965-03-2 ]
[ 2440-22-4 ]
[ 1552277-81-2 ]

Yield	Reaction Conditions	Operation in experiment
86%	In dichloromethane; for 48h;Reflux;	[Pd(PPh3)2Cl2] (0.175 g, 0.25 mmol) was added to Hhmbt(0.057 g, 0.25 mmol) in CH2Cl2 (20 mL). The reaction mixture washeated under reflux for 48 h. The yellow precipitate was filteredoff, washed with CH2Cl2 and dried in vacuo. Yield: 0.20 g; 86%. ElementalAnal.: Calcd.: C, 59.2; H, 4.0; N, 6.7; Cl, 5.7; Pd, 16.9 (C31-ClH25N3OPd); Found: C, 59.4; H, 4.1; N, 6.6; Cl, 5.6; Pd, 16.8%.Conductivity data (103 M in DMF): KM = 7.0 ohm1. IR (cm1):m(CN), 1586; m(CO), 1307; m(N-N), 1158; m(Pd-O), 532; m(Pd-N), 438. Raman (cm1): m(CN), 1585; m(CO), 1309; m(N-N),1160; m(Pd-O), 530; m(Pd-N), 434; m(Pd-P), 301; m(Pd-Cl), 199.UV-visible (nm): 280, 358, 388. MS (m/z): 628.2 (Calcd. 627.9).

Reference： [1]Journal of Molecular Structure,2014,vol. 1059,p. 193 - 201

34
[ 13965-03-2 ]
[ 1551310-73-6 ]
C₃₅H₃₁N₄O₂PPdS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	With triethylamine; at 20℃; for 2h;	The reaction of H2L ligand with PdCl2(PPh3)2, in toluene, in presence of Et3N, in 1:1 M ratios over 2h at room temperature led to the formation of an orange solution which was filtered and left to stand at ambient temperature for two days. The solid formed was filtered, washed several times with hot water, recrystallizated from DMSO and finally dried in vacuo. Yield (35%), mp>250C. Elemental analysis found, C, 56.7; H, 4.6, N, 7.1; C35H31N4O2SPPd·DMSO requires C, 56.5; H, 4.7, N, 7.1%. IR (KBr pellet): n/cm-1 3418 (s, NH); 3048 (w, PPh3); 1685 (s, CO); 1591 (s, CN); 1537 (s, CN-thioamide I); 1076 (w, PPh3); 798 (vw, CS-thioamide IV). 1H NMR (300.14MHz, DMSO-d6): delta (ppm) 9.40 (s, 4NH), 7.65-7.45 (m, H12, H13, H15, H16 and -PPh3 aromatic protons); 7.00 (d, H2); 6.85 (d, H3); 3.70 (s, H17); 2.55 and 2.50 (s, H6 and H9).

Reference： [1]Journal of Organometallic Chemistry,2014,vol. 751,p. 374 - 378

35
[ 13965-03-2 ]
[ 201360-06-7 ]
[ 1620144-07-1 ]

Yield	Reaction Conditions	Operation in experiment
55%	With triethylamine; In toluene; at 20℃; for 20h;	The reaction of H2L ligandwith PdCl2(PPh3)2, in toluene, in presenceof Et3N, in 1:1 molar ratios over 20 h at room temperature led to theformation of an orange solution which was filtered and left to stand atambient temperature for two days. The brown solid formedwas filtered,washed several times with hot water, diethyl ether and finally dried invacuo.Yield (55%),mpN 250 C. Elemental analysis found, C, 43.35; H, 3.35,N, 15.10; S, 10.05; C23H19N7S2Cl2Pd requires C, 43.51; H, 3.02, N, 15.44;S, 10.10%.MS(FAB+withmNBAmatrix)m/z 636 for [PdL+H]+. IR(KBrpellet): upsilon/cm-1 3243 (s, NH); 1595 (s, CN); 830, 804 (vw) (CSthioamideIV); 603 (pyridine ring). 1H NMR (300 MHz, d6-DMSO,ppm), delta = 10.75, 10.18 [s, 4NH, 2H]; 8.43-8.10 [m, CH-pyridine, 3H];7.71-7.34 (m, aromatic-thiosemicarbazide, 8H); 2.72, 2.62 (s, CH3-diacetylpyridine, 6H). UV/VIS (DMSO): lambda/nm 267, 340, 410, 470.Recrystallization fromDMSO led to the isolation of orange crystals of[PdL] · DMSO that were suitable for X-ray-diffraction.

Reference： [1]Journal of Inorganic Biochemistry,2014,vol. 138,p. 16 - 23

36
[ 13965-03-2 ]
[ 3608-75-1 ]
C₂₅H₂₂N₄PPdS⁽¹⁺⁾*Cl^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With triethylamine; In ethanol; for 5h;Reflux;	Complex 1 2-Formylpyridine thiosemicarbazone (26 mg, 0.14 mmol) was dissolved in warm ethanol (30 mL) and triethylamine (14 mg, 0.14 mmol) was added to it, followed by [Pd(PPh3)2Cl2] (100 mg, 0.14 mmol). The mixture was then refluxed for 5 h to yield a yellowish-brown solution. The solvent was evaporated and the solid mass, thus obtained, was subjected to purification by thin layer chromatography on a silica plate. With 1:3 acetonitrile-benzene as the eluant, an orangish-yellow band separated, which was extracted with acetonitrile. Evaporation of the acetonitrile extract gave complex 1 as an orangish-yellow crystalline solid. Yield: 68%. Anal. Calc. for C25H22N4PSClPd: C, 51.47; H, 3.77; N, 9.61. Found: C, 51.53; H, 3.72; N, 9.65%. Mass spectral data (ESI, positive mode, CH3CN): m/z 547 for [1-Cl]+. LambdaM: 145 -1 cm2 M-1. 1H NMR (300 MHz, CDCl3) 1 : 5.73 (s, NH2), 7.19 (t, 1H, J = 9.0), 7.38 (s, 1H), 7.58-7.72 (PPh3), 7.87 (d, 1H, J = 8.0), 8.06 (t, 1H, J = 8.5), 8.16 (d, 1H, J = 9.0). 31P NMR (300 MHz, CDCl3): 43.04 ppm. IR (cm-1): 1646, 1602, 1562, 1480, 1458, 1434, 1375, 1318, 1255, 1179, 1098, 1020, 997, 752, 722, 697, 532, 508.

Reference： [1]Inorganica Chimica Acta,2015,vol. 425,p. 67 - 75

37
[ 13965-03-2 ]
2-(1-(pyridin-2-yl)ethylidene)hydrazinecarbothioamide [ No CAS ]
C₂₆H₂₄N₄PPdS⁽¹⁺⁾*Cl^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With triethylamine; In ethanol; for 5h;Reflux;	General procedure: 2-Formylpyridine thiosemicarbazone (26 mg, 0.14 mmol) wasdissolved in warm ethanol (30 mL) and triethylamine (14 mg,0.14 mmol) was added to it, followed by [Pd(PPh3)2Cl2] (100 mg,0.14 mmol). The mixture was then refluxed for 5 h to yield a yellowish-brown solution. The solvent was evaporated and the solidmass, thus obtained, was subjected to purification by thin layerchromatography on a silica plate. With 1:3 acetonitrile-benzeneas the eluant, an orangish-yellow band separated, which wasextracted with acetonitrile. Evaporation of the acetonitrile extractgave complex 1 as an orangish-yellow crystalline solid. Yield:68%.

Reference： [1]Inorganica Chimica Acta,2015,vol. 425,p. 67 - 75

38
[ 13965-03-2 ]
[ 82766-13-0 ]
C₃₁H₂₆N₄PPdS⁽¹⁺⁾*Cl^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With triethylamine; In ethanol; for 5h;Reflux;	General procedure: 2-Formylpyridine thiosemicarbazone (26 mg, 0.14 mmol) wasdissolved in warm ethanol (30 mL) and triethylamine (14 mg,0.14 mmol) was added to it, followed by [Pd(PPh3)2Cl2] (100 mg,0.14 mmol). The mixture was then refluxed for 5 h to yield a yellowish-brown solution. The solvent was evaporated and the solidmass, thus obtained, was subjected to purification by thin layerchromatography on a silica plate. With 1:3 acetonitrile-benzeneas the eluant, an orangish-yellow band separated, which wasextracted with acetonitrile. Evaporation of the acetonitrile extractgave complex 1 as an orangish-yellow crystalline solid. Yield:68%.

Reference： [1]Inorganica Chimica Acta,2015,vol. 425,p. 67 - 75

39
[ 13965-03-2 ]
[ 26042-63-7 ]
bis[bis(triphenylphosphine)-μ-chloro-palladium(II)] bis(hexafluorophosphate) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	In dichloromethane; at 20℃; for 16h;Inert atmosphere; Schlenk technique; Darkness;	500mg (0.712mmol) of Pd(PPh3)2Cl2 were suspended in 100mL dichloromethane and 180.1mg (0.712mmol, 1eq.) AgPF6 was added. The reaction mixture was stirred at room temperature under the exclusion of light. After 16h, the solvent was evaporated and the residue was resolved in acetonitrile, filtered and concentrated to 30mL. By adding 200mL of diethyl ether, the desired product [Pd(PPh3)2(mu-Cl)]]2(PF6)2 1b precipitates out of solution. The solid was filtered off and dried under vacuum to yield 213.5mg (0.263mmol, 74%) of [Pd(PPh3)2(mu-Cl)]2(PF6)2 1b. Slow diffusion of diethylether into a CH3CN solution of 2 yielded crystals suitable for XRD. 1H NMR (400MHz, CD3CN): delta [ppm]=7.27-7.80 (m, 60H, CHPh). 31P NMR (162MHz, CD3CN):-144.62 (sep., PF6), 21.98 (s,PPh3). Elemental analysis calc. for C72H60Cl2F12P6Pd2: C 53.29, H 3.73; found: C 53.00, H 3.63

Reference： [1]Journal of Organometallic Chemistry,2015,vol. 775,p. 130 - 136

40
[ 13965-03-2 ]
[ 603-35-0 ]
[ 7550-35-8 ]
[ 25044-96-6 ]

Yield	Reaction Conditions	Operation in experiment
96%	In chloroform; isopropyl alcohol; at 20℃; for 2h;	To a suspension of trans-[PdCl2L2] (0.10mmol) in 5mL of iPrOH/CHCl3 (1/1) a solution of LiBr (2.4mmol) and PPh3 (0.2mmol) in 5mL of iPrOH was added under stirring at room temperature. After two hours, the solution was concentrated to half the volume and 5mL of Et2O was added. The microcrystalline solid was filtered off, washed several times with iPrOH and Et2O and dried under vacuum. Yield: 96%. Elem. anal. calcd for C36H30Br2P2Pd: C, 54.68; H, 3.82; found: C, 53.61; H 3.92. NMR: 1H 7.75-7.41 (m, 30H, Ph), 31P{1H} 23.2 (s).

Reference： [1]Journal of Organometallic Chemistry,2014,vol. 767,p. 72 - 77

41
[ 13965-03-2 ]
[ 97671-41-5 ]
[PdCl(μ-Te(phenyl))P(phenyl)₃]₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	In tetrahydrofuran; at 65℃; for 2h;Inert atmosphere;	General procedure: To a solution of 0.351 g (0.5 mmol) of bis(diphenyl-2-pyridylphosphine)palladium(II) dichloride in 10 mL THF, a suspension of 0.127 g (0.25 mmol) of (PhTe)2Hg in 5 mL THF was added very slowly. Thereafter the mixture was stirred and heated in an oil bath at 65 C for 2 h until the dissolution of (PhTe)2Hg occurred. To the orange translucent solution, 2 mL of diethyl ether were added. After 3 days the slow evaporation of the solvent afforded orange-yellow crystals suitable for X-ray analysis.

Reference： [1]Polyhedron,2015,vol. 85,p. 565 - 569

42
[ 13965-03-2 ]
[ 97671-41-5 ]
[PdCl(μ-TePh)PPh₃]₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	In tetrahydrofuran; at 65℃; for 2h;	General procedure: To a solution of 0.351g (0.5mmol) of bis(diphenyl-2-pyridylphosphine)palladium(II) dichloride in 10mL THF, a suspension of 0.127g (0.25mmol) of (PhTe)2Hg in 5mL THF was added very slowly. Thereafter the mixture was stirred and heated in an oil bath at 65C for 2h until the dissolution of (PhTe)2Hg occurred. To the orange translucent solution, 2mL of diethyl ether were added. After 3days the slow evaporation of the solvent afforded orange-yellow crystals suitable for X-ray analysis. Yield: 0.101g, 33.4% based on (PhTe)2Hg.

Reference： [1]Polyhedron,2015,vol. 85,p. 565 - 569

43
[ 13965-03-2 ]
[ 73703-08-9 ]
C₃₆H₂₆ClN₂O₂PPd [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With triethylamine; In ethanol; N,N-dimethyl-formamide;Inert atmosphere; Reflux;	The reaction was carried out in anhydrous conditions under nitrogen atmosphere and the new palladium benzhydrazone complex was prepared by the following general procedure: To a ethanol solution (20 mL) of [PdCl2(PPh3)2] (140.35 mg, 0.20 mmol) was added benzhydrazone ligand (64.95 mg, 0.20 mmol) and triethylamine (1.0 mL) as base. The reaction mixture was reflux for 3 h and the progress of the reaction was monitored using TLC. During the course of the reaction, orange solid was precipitated, which was filtered and dried under vacuum.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 4170 - 4174

44
[ 13965-03-2 ]
1-pyrenaldehyde-4-methyl-3-thiosemicarbazone [ No CAS ]
C₃₇H₂₉ClN₃PPdS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With triethylamine; In toluene; for 3h;Reflux;	Solid trans-[Pd(PPh3)2Cl2] (140 mg, 0.2 mmol) was added to a suspension of HL (64 mg, 0.2 mmol) and triethylamine (0.3 mL) in toluene (20 mL). The reaction mixture was heated under reflux for 3 h. The orange solution was then cooled to room temperature and filtered. The filtrate was concentrated to about 3 mL and n-hexane was added whereby orange solid separated out. The obtained solid was reprecipitated from CH2Cl2/n-hexane mixture and dried in air. Yield was 96 mg (67%). Anal. Calcd for C37H29ClN3PPdS: C, 61.67; H, 4.06; N, 5.83. Found: C, 61.56; H, 4.12; N, 5.75. ESI-MS Found (calcd) m/z {M+H}+: 720.0619 (720.0622). Selected IR bands (KBr, cm-1): 1577 C=N, 514, 700, 750 Pd-PPh3. 1H NMR (400 MHz, (CD3)2SO) ( ppm): 10.22 (s, 1H, CH=N), 8.95 (d, J = 8.4 Hz, 1H, ArH), 8.79 (s, 1H, NHMe), 8.53-8.48 (m, 3H), 8.33-8.25 (m, 6H), 8.21-8.18 (m, 1H), 8.05 (t, J = 7.6 Hz, 1H), 7.70 (d, J = 7.2 Hz, 3H), 7.38-7.34 (m, 4H), 7.16-7.12 (m, 5H), 3.2 (d, J = 4.4 Hz, 3H, NCH3). 13C NMR (100 MHz, (CD3)2SO) ( ppm): 166.50 (C-S), 153.02 (C=N), 137.58, 132.21, 131.36, 131.06, 130.63, 129.02, 128.61, 128.11, 127.90, 127.57, 126.93, 126.42, 126, 11, 125.57, 124.65, 124.43, 122.09, 31.65. 31P NMR (160 MHz, (CD3)2SO) ( ppm): 28.0

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 5252 - 5256

45
[ 13965-03-2 ]
[ 78593-40-5 ]
bis(triphenylphosphine)bis(quinolin-3-yl-ethynyl)palladium [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With copper(l) iodide; In diethylamine; for 3h;Reflux;	A suspension of Pd(PPh3)2Cl2 (0.20mmol, 140mg) and CuI (2mg) in anhyd diethylamine was treated under a nitrogen atmosphere with 3-ethynylquinoline (1.00mmol, 153mg) and then heated to 3h at reflux temperature. The resulting precipitate was then filtered off, washed with ethyl acetate, ethanol and water, respectively, and dried. Yield: 121mg (0.13mmol, 65%), orange solid. Mp: 202.6C (dec). IR (ATR, cm-1) 2103, 1479, 1433, 1098, 902, 743, 702, 687, 612, 521, 513, 499, 445. The complex is insoluble in all NMR solvents which we tested.

Reference： [1]Tetrahedron,2015,vol. 71,p. 6665 - 6671

46
[ 13965-03-2 ]
[ 78593-40-5 ]
bis(triphenylphosphine)bis((1-methylquinolinium-3-yl)ethynyl)palladium(II) hexafluorophosphate [ No CAS ]

Reference： [1]Tetrahedron,2015,vol. 71,p. 6665 - 6671

47
[ 13965-03-2 ]
[ 33513-42-7 ]
[ 3878-45-3 ]
[ 306770-84-3 ]
[Pd₂(2-(5,6-dimethyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-2-yl)-N-phenylhydrazinecarbothioamide-2H)₂(PPh₃)₂]*triphenylphosphine sulfide*3(dimethylformamide) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In chloroform; for 1h;Heating;	General procedure: 65.5 mg (0.25 mmol) of PdCl2(PPh3)2 were dissolved in 15 ml of CHCl3 under heating. To the obtained yellow solution was added H2L solution (86.7 mg 0.25 mmol in 10 ml of DMF). The obtained light ruby solution was stirred with heating for 1 h and then was left for crystallization by slow solvent evaporation. In a few days light pink needle like crystals of monoclinic modification of 1a, [Pd(HL)PPh3Cl]·2DMF, formed which in a week completely transformed into fine light ruby prismatic crystals of more stable triclinic modification 1b, [Pd(HL)PPh3Cl]·DMF, both of them were investigated by single crystal X-ray diffraction. Crystals were filtered off, washed with cold C2H5OH and dried on the air.

Reference： [1]Journal of Molecular Structure,2015,vol. 1102,p. 161 - 169

48
[ 13965-03-2 ]
[ 149-30-4 ]
[Pd(PPh₃)(mbt)Cl] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With potassium hydroxide; In methanol; dichloromethane; for 48h;Reflux;	General procedure: A suspension of [M(PPh3)2Cl2] (0.25 mmol) in CH2Cl2 (15 mL)was added to Hmbt (0.042 g, 0.25 mmol) in methanolic solution containing KOH (0.25 mmol; 20 mL). The reaction mixture was heated under reflux for 48 h. The produced brown precipitate was filtered off, washed with CH2Cl2 and dried in vacuo.

Reference： [1]Inorganica Chimica Acta,2016,vol. 441,p. 20 - 23

49
[ 13965-03-2 ]
3,5-diacetyl-1,2,4-triazol mono(4-phenylthiosemicarbazone) [ No CAS ]
C₃₁H₂₇N₆OPPdS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With lithium hydroxide monohydrate; In ethanol; at 20℃; for 2h;	General procedure: 0.33 mmol of the corresponding MCl2(PPh3)2 metallic salt (0.23 g for M = Pd and 0.33 g for M = Pt) was added to an ethanolic solution (20 mL) of 3,5-diacetyl-1,2,4-triazol mono(4-phenylthiosemicarbazone) ligand (0.33 mmol, 0.10 g) and LiOH·H2O (0.66 mmol, 0.028 g). The reaction mixture was stirred for 2 h at room temperature and then, the solid formed was filtered, washed with ethanol and diethyl ether and finally dried in vacuo. 2.3.3. [Pd(HL)(PPh3)]Yield (60%), mp 196 C. Elemental analysis found, C, 55.55; H,4.30; N, 12.80; S, 5.00; C31H27N6SOPPd requires C, 55.65; H, 4.05;N, 12.60; S, 4.80%. MS (ESI+ with MeOH + HCOOH 0.1%): m/z 669for [C31H27N6SOPPd+H]+. IR (KBr pellets): m/cm1 3166 (s, NH);1696 (s, CO); 1599 (s, CN); 1097 (s, PC). 1H NMR (300.14 MHz,DMSO-d6): d (ppm) 10.05 (s, NH, 1H); 7.70-7.01 (m, aromatic protons);2.51 and 2.50 (s, CH3, 3H). UV/Vis (DMSO): k/nm 260, 320,366, 455. Crystallization in CH3CN allowed us to isolate single crystals,which were studied by X-ray diffraction techniques.

Reference： [1]Inorganica Chimica Acta,2016,vol. 445,p. 62 - 69

50
[ 13965-03-2 ]
[ 1761-56-4 ]
N-(2-oxidophenyl)salicylideneiminatotriphenylphosphiepalladium(II) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	In ethanol; for 24h;Inert atmosphere;	General procedure: Complexes 1 and 2 were prepared by refluxing equimolarethanolic solutions of Schiff base (H2L1 or H2L2) and PdCl2(PPh3)2 in250 mL two neck flask under nitrogen for 24 h. The red solid wasfiltered off, washed with ethanol, dried in air and stored in vacuumdesiccator (Scheme 1).where PPh3 triphenylphosphine, Y O for1, S for 2.

Reference： [1]Journal of Molecular Structure,2016,vol. 1118,p. 250 - 258

51
[ 13965-03-2 ]
[ 3449-05-6 ]
N-(2-sulfidophenyl)salicylideneiminato triphenylphosphinepalladium(II) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	In ethanol; for 24h;Inert atmosphere;	General procedure: 2.2.1 N-(2-oxidophenyl)salicylideneiminato triphenylphosphiepalladium(II) (1) Yield: 83%. mp 254 C, upsilonmax/cm-1 1595 (-CH=N), 1338 (C-O), 545 (Pd-O), 412 (Pd-N) deltaH 7.9-6.6 (m, 23 H, Ar-H), 8.8 (s, 1H, -CH=N-). deltaC 169.0 (C-O),163.5 (C=N),147.6 (C-P), 138.1-114.5(Ar-C), deltaP 22.8. Calc. for C31H24NO2 PPd: C 64.2, H 4.1, N 2.4. Found: C 64.3, H 4.1, N 2.3%.

Reference： [1]Journal of Molecular Structure,2016,vol. 1118,p. 250 - 258

52
[ 13965-03-2 ]
{(E)-2-[1-(3-acetyl-1H-1,2,4-triazol-5-yl)ethylidene]-N-(4-chlorophenyl)hydrazidecarbothioamide} [ No CAS ]
C₃₁H₂₆ClN₆OPPdS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	With lithium hydroxide monohydrate; In ethanol; at 20℃; for 2h;	General procedure: Were obtained by reaction of the corresponding MCl2(PPh3)2metallic salt (M = Pd, Pt) with H3L2 ligand in ethanol, in the presenceof two equivalents of LiOH*H2O, in 1:1 molar ratios. The reactionmixture was stirred for 2 h at room temperature and then, thesolid formed was filtered, washed with ethanol and diethyl etherand finally dried in vacuo.

Reference： [1]Polyhedron,2016,vol. 109,p. 161 - 165

53
[ 13965-03-2 ]
[ 529-84-0 ]
C₄₆H₃₆O₄P₂Pd [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; for 36h;Reflux;	General procedure: H2mesc (0.096 g, 0.5 mmol) was added to a suspension of [M(PPh3)2Cl2] (M(II) = Pd, Pt) (0.5 mmol) in dichloromethane (10 mL). The mixture was heated under reflux for 36 h. The yellow precipitate was filtered off, washed with dichlromethane and air dried. For [Pd(PPh3)2(mesc)]: Anal. Calc. For C46H36O4PdP2: C, 67.3; H,4.4; Pd, 13.0percent, Found: C, 67.4, H, 4.4; Pd, 13.0percent. Conductivity data (10-3 M in DMSO): KM = 3.0 Ohm1 cm2 mol1. IR (cm1);m(CO) 1664; m(CAC) 1494; m(CAO) 1260; m(PdAO) 517. 1H NMR (d6-DMSO/TMS, ppm), d: CH3, 3.33; H(3), 6.65; H(8), 5.82;H(5), 6.19. ESI-MS: m/z: 821.1 (Calcd 820.4) [Pd(PPh3)2(mesc)]+;630.0 (Calcd 630.4) [Pd(PPh3)2]+; 367.5 (Calcd 368.4) [Pd(PPh3)]+.

Reference： [1]Inorganica Chimica Acta,2014,vol. 423,p. 132 - 143

54
[ 13965-03-2 ]
[ 1004-76-8 ]
[Pd(dahmp)(PPh₃)Cl] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	In dichloromethane; for 72h;Reflux;	Solid [Pd(PPh3)2Cl2] (0.18 g, 0.25 mmol) was added to Hdahmp(0.04 g, 0.25 mmol) in DCM (10 mL). The reaction mixture washeated under reflux for 72 h. A yellow precipitate was obtainedwhich was filtered off, washed with hot CH2Cl2 and air-dried.Yield: 72%. Anal. Calc. for C22H20ClN4OPPdS: C, 47.1; Cl, 6.3; H,3.6; N, 10.0; S, 5.7; Pd, 19.0. Found: C, 47.1; Cl, 6.5; H, 3.8; N,10.1; S, 5.6; Pd, 19.1%. Conductivity data (103 M in DMF):KM = 8.0 ohm1 cm2 mol1.

Reference： [1]Inorganica Chimica Acta,2014,vol. 423,p. 144 - 155

55
[ 13965-03-2 ]
[ 41377-38-2 ]
C₃₂H₂₄BrN₂O₃PPd [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With triethylamine; In methanol; dichloromethane; for 1h;Reflux;	To awarmmethanolic solution (25 ml) of H2L (0.0335 g; 0.1mmol),dichloromethane solution of [PdCl2(PPh3)2] (0.0701 g, 0.1 mmol) wasadded and followed by two drops of triethylamine. The reaction mixturewas refluxed 1 h and kept at room temperature for crystallization. Needlelike orange red crystals suitable for X-ray studies were obtained onslowevaporation. Yield: 79%,melting point: 221 C. Elemental analysis:found (calculated) (%) C32H24BrN2O3PPd: C, 52.56 (54.76); H, 3.76(3.45); N, 3.90 (3.99). Selected IR bands (cm-1): 1590 nu(C_N); 1353nu(enolic CO); 1423, 1095, 690 (for PPh3). UV-vis (DMSO), lambdamax(nm) (epsilonM-1 cm-1): 302 (9170), 368 (8221) (intra-ligand transitions);409 (7253), 424 (6560) (LMCT). 1H NMR (DMSO-d6): delta 8.53 (s, 1H, H-C=N), delta 9.93 (s, 1H, p-OH), delta 7.70 (d, 1H, aromatic CH), delta 7.68 (d, 1H,aromatic CH), delta 7.66 (d, 1H, aromatic CH), delta 7.65 (d, 2H, aromatic CH), delta7.63 (d, 2H, aromatic CH), delta 7.32 (d, 6H, aromatic CH), delta 6.75 (d, 6H, aromaticCH), delta 6.64 (d, 3H, aromatic CH), 13C NMR: delta 158 (CO), delta 171(C_N), delta 144.61, 134.65, 134.55, 133.21, 132.31, 131.16, 130.78,130.61, 128.78, 128.31, 127.31, 126.22, 118.89, 114.21 (aromatic). 31PNMR: delta 20.8.

Reference： [1]Journal of Photochemistry and Photobiology B: Biology,2016,vol. 163,p. 1 - 13

56
[ 13965-03-2 ]
[ 731794-67-5 ]
Pd(pyridoxal thiosemicarbazone)PPh3 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	In ethanol; dichloromethane; for 4h;Reflux;	General procedure: All the new metal complexes were prepared according to the following general procedure. Ethanolic solution of pyridoxal N(4)-substituted thiosemicarbazone hydrochloride ligand (1 mmol) was added to [PdCl2(PPh3)2] (1 mmol) in dichloromethane. The resulting yellow color solution was refluxed for 4 h. A dark yellow colored crystalline powder was obtained on slow evaporation, which was filtered off, washed with ethanol, and dried under vacuo. 2.2.1 Synthesis of [Pd(L1)PPh3] (1) The complex was synthesized from [PdCl2(PPh3)2] (0.701 g; 1 mmol) and L1 (0.276 g; 1 mmol). Yield: 0.482 g, 75%; Color: yellow solid; M. p.: 224 C; Anal. Calc. for C27H26ClN4PdO2PS (643.43 g, mol-1): C, 50.40; H, 4.07; N, 8.71; S, 4.98. Found: C, 50.21; H, 4.69; N, 8.22; S, 4.33%. IR (KBr, cm-1): 3433(s) nu(CH2OH), 3328, 3290(m) nu(-NH-R), 2760(m) nu(NH+), 1628(s) nu(C=N), 1600(s) nu(C=N), 760(s) nu(C-S), 1436, 1092, 695 nu(PPh3). UV-Vis (CH3OH, lambdamax/nm): 253, 297 (intra-ligand transitions), 428 (LMCT). 1H NMR (300 MHz, DMSO-d6, delta): 8.61 (s, 1H, CH=N), 8.30 (s, 2H, NH2); 7.86 (s, 1H, Py); 7.11-7.86 (m, 15H, PPh3); 5.32 (s, 1H, OH), 4.70 (s, 2H, CH2), 2.49 (s, 3H, CH3). 31P NMR (300 MHz, DMSO-d6, delta): 27.8. ESI-MS, m/z: 606.1 [M-HCl]+.

Reference： [1]Polyhedron,2016,vol. 119,p. 300 - 306

57
[ 13965-03-2 ]
[ 955953-04-5 ]
Pd(pyridoxal N-methyl thiosemicarbazone)PPh3 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	In ethanol; dichloromethane; for 4h;Reflux;	General procedure: All the new metal complexes were prepared according to the following general procedure. Ethanolic solution of pyridoxal N(4)-substituted thiosemicarbazone hydrochloride ligand (1 mmol) was added to [PdCl2(PPh3)2] (1 mmol) in dichloromethane. The resulting yellow color solution was refluxed for 4 h. A dark yellow colored crystalline powder was obtained on slow evaporation, which was filtered off, washed with ethanol, and dried under vacuo.

Reference： [1]Polyhedron,2016,vol. 119,p. 300 - 306

58
[ 13965-03-2 ]
[ 15017-21-7 ]
C₃₆H₂₇N₂O₂PPd [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With triethylamine; In methanol; chloroform;Reflux;	General procedure: To a warm methanolic solution (20-30 mL) of appropriate ligands(H2L1-H2L3) (1 equiv.) was added a chloroform solution of[PdCl2(PPh3)2] (1 equiv.) followed by two drops of triethylamine.Then the reaction mixture was refluxed for 8-10 h and kept atroom temperature for crystallization. Needle like reddish browncrystals suitable for X-ray studies were obtained on slow evaporationover 45-60 days.[Pd(L1) (PPh3)] (complex 1) Yield: 85% (112 mg). M. p.232-234 C. Elemental analysis (%) calculated for C36H27N2O2PPd;C, 65.81; H, 4.14; N, 4.26. Found (%) C, 65.82; H, 4.15; N, 4.27.UV-visible (solvent: DMSO, nm): 303, 325, 341, 354. Selected IRbands (KBr, n in cm-1): 1581 (C-N=N-C), 1528 (C]N), 1433(PPh3), 1260 (imidolate -N=C-O), 1185 (naphtholate C-O). 1HNMR (CDCl3, delta ppm) 9.86 (s, 1H), 9.30 (d, J 8 Hz, 4H), 7.81 (s, 2H),7.55 (d, J 7.6 Hz, 2H), 7.23-7.36 (m, 10H), 7.15 (t, J 5.8 Hz, 6H),6.44 (d, J 15.6 Hz, 2H); 13C NMR (CDCl3, delta ppm) 183.5, 167.5, 145.2,142.2, 138.5, 134.7, 129.4, 128.3, 127.0, 124.4, 123.9, 120.7, 119.3,118.4, 112.0.

Reference： [1]Journal of Organometallic Chemistry,2016,vol. 824,p. 7 - 14

59
[ 13965-03-2 ]
[ 73703-08-9 ]
C₃₆H₂₆ClN₂O₂PPd [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With triethylamine; In methanol; chloroform;Reflux;	General procedure: To a warm methanolic solution (20-30 mL) of appropriate ligands(H2L1-H2L3) (1 equiv.) was added a chloroform solution of[PdCl2(PPh3)2] (1 equiv.) followed by two drops of triethylamine.Then the reaction mixture was refluxed for 8-10 h and kept atroom temperature for crystallization. Needle like reddish browncrystals suitable for X-ray studies were obtained on slow evaporationover 45-60 days.[Pd(L1) (PPh3)] (complex 1) Yield: 85% (112 mg).

Reference： [1]Journal of Organometallic Chemistry,2016,vol. 824,p. 7 - 14

60
[ 13965-03-2 ]
[ 95523-63-0 ]
C₃₆H₂₆N₃O₄PPd [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With triethylamine; In methanol; chloroform;Reflux;	General procedure: To a warm methanolic solution (20-30 mL) of appropriate ligands(H2L1-H2L3) (1 equiv.) was added a chloroform solution of[PdCl2(PPh3)2] (1 equiv.) followed by two drops of triethylamine.Then the reaction mixture was refluxed for 8-10 h and kept atroom temperature for crystallization. Needle like reddish browncrystals suitable for X-ray studies were obtained on slow evaporationover 45-60 days.[Pd(L1) (PPh3)] (complex 1) Yield: 85% (112 mg).

Reference： [1]Journal of Organometallic Chemistry,2016,vol. 824,p. 7 - 14

61
[ 13965-03-2 ]
4-hydoxybenzoic acid (5-chloro-2-hydroxybenzylidene)hydrazide [ No CAS ]
C₃₂H₂₄ClN₂O₃PPd [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With triethylamine; In methanol; dichloromethane; for 1h;Reflux;	For the preparation of 2, a methanolic solution (20 cm3) of H2L (1) (0.0290 g; 0.1 mM) was mixed with dichloromethane (20 cm3) solution of [PdCl2(PPh3)2] (0.0701 g; 0.1 mM) and twodrops of triethylamine. The mixture was refluxed for 1 h. An orangecoloured precipitate was formed during this period. The reactionmixture was then cooled to room temperature, and the solid compoundwas filtered. It was washed with methanol and dried undervacuum. The single crystals of 2, grown from methanol/DMF werefound to be suitable for X-ray diffraction. C32H24ClN2O3PPd (2):Yield: 81%, MP: 255 C, Anal. calcd. (%): C, 58.46; H, 3.68; N,4.26; Found (%): C, 58.51; H, 3.69; N, 4.25. Selected IR bands(cm1): 1590 m(CN); 1356 m(enolic CAO); 1434, 1049, 694 (forPPh3). UV-vis (DMSO), kmax(nm) (e M1 cm1): 275 (11303), 313(10393) (intra-ligand transitions); 412 (7848) (LMCT). 1H NMR(DMSO-d6): d 8.53 (s, 1H, H-CN), d 9.92 (s, 1H, p-OH), d 6.62-7.76 (m, 22H, aromatic).

Reference： [1]Inorganica Chimica Acta,2016,vol. 453,p. 562 - 573

62
[ 1945-84-2 ]
[ 13965-03-2 ]
bis(triphenylphosphine)palladium(II)(pyridin-2-yl-ethynyl)chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%		A sample of 73mg (0.71mmol) in 4mL of anhydrous THF was cooled to -78C and then treated with 0.45mL (46mg, 0.72mmol) of a 15% solution of nBuLi in hexane and 204mg (0.29mmol) of PdCl2(PPh3)2. After stirring for 4h at that temperature, the suspension was allowed to warm to rt, and stirring was continued for 1d. Then, the solvent was distilled off in vacuo and the crude reaction product was recrystallized form EtOAc/MeOH. The resulting crystals were washed with MeOH and EtOAC, and dried in vacuo. Yield: 77mg (0.10mmol, 34%) of a brown powder. 1H NMR (400MHz, DMSO-d6: delta=8.20-8.18 (m, 1H), 7.77-7.71 (m, 12H), 7.64-7.53 (m, 6H), 7.46-7.41 (m, 12H), 7.33-7.29 (m, 1H), 6.94-6.91 (m, 1H), 6.12-6.10 (m, 1H); due to the limited solubility, no 13C NMR spectrum was obtained. IR (ATR): nu nu =3333, 3050, 2920, 2196, 2109, 1580, 1554, 1516, 1479, 1458, 1432, 1421, 1329, 1307, 1236, 1182, 1147, 1118, 1092, 1071, 1046, 1026, 997, 987, 774, 742, 721, 703, 691, 629, 617, 577, 540, 519, 506, 498, 453, 445, 437, 428, 418cm-1. ESI-MS (5eV): m/z (%)=769.0 (10) [M++H+]. Due to the limited solubility, no HRMS could be obtained.

Reference： [1]Tetrahedron,2016,vol. 72,p. 7906 - 7911

63
[ 13965-03-2 ]
[ 24090-94-6 ]
[Pd(2-((1-naphthalenyl)methylene)-N-phenylhydrazinecarbothioamide)Cl(PPh₃)] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	In ethanol; dichloromethane; at 20℃;	To a solution of the Schiff base, HL, (0.20 mmol) in dichloromethane (20 mL), an ethanolic solution (20 mL) of [Pd(PPh3)2Cl2] (0.20 mmol) was slowly added. The reaction mixture was allowed to stand for 3-5 days at room temperature. Orange solid was precipitated, which was filtered, washed with diethyl ether (5 mL) and dried (Scheme 1).

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 405 - 409

64
[ 13965-03-2 ]
[ 583-39-1 ]
[ 7732-18-5 ]
[Pd^II₂(μ-κ²:N,S-bzimS)₂(κ¹-S-bzimS)(PPh₃)₃]Cl₂•H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With triethylamine; In acetonitrile; for 6h;Reflux;	To the solution of PdCl2(PPh3)2 (0.050 g, 0.07 mmol) dissolvedin 10 mL of CH3CN, bzimSH (0.021 g, 0.14 mmol) was added followedby Et3N base (0.5 mL). The solution became turbid and yellowishorange in color. Then the refluxing was done for 6 h. Thecolor of the reaction mixture became orange and was filtered.The filtrate was evaporated using rotary evaporator until a solidwas obtained. It was treated with acetone which dissolved thecomplex leaving behind Et3NH+Cl, white solid. The acetone solutionwas filtered to remove Et3NH+Cl. To it was added 4 mLdichloromethane-methanol (1:1, v/v) mixture and left to evaporateat room temperature. The orange colored crystals of compound2 were formed in a period of 10-15 days (67%, m.p 218-220 C). Anal. Calc. for C75H61ClN6P3Pd2S32H2O (1519.67): C,59.22; H, 4.01; N, 5.53. Found: C, 59.80; H, 4.36; N, 5.52%. IRbands(KBr, cm1): nu(O-H), 3393m (b); m(C-H), 3051m, 2963w; nu(C-C) + nu(C-N) + delta(C-H), 1618s, 1479m, 1433s, 1391s, 1263m,1226w;, 1182 w; nu(P-CPh), 1096s; nu(C-S) 1022s; 802m, 741s,691s, nu(Pd-N), 523s; 422w. ESI Mass could not be recorded dueto poor solubility.

Reference： [1]Polyhedron,2017,vol. 127,p. 25 - 35

65
[ 872-35-5 ]
[ 13965-03-2 ]
[ 7732-18-5 ]
[Pd(κ¹:S-1,3-imidazoline-2-thione)₄]Cl₂•2H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With triethylamine; In acetonitrile;Reflux;	To a suspension of PdCl2(PPh3)2 (0.05, 0.071 mmol) in 10 mL ofCH3CN, imzSH (0.014 g, 0.14 mmol) was added in presence of Et3Nbase (0.5 mL). The solution became turbid orange and the contents were refluxed for 5-6 h. The filtrate was evaporated using rotaryevaporator until a solid was obtained. The solid obtained was dissolvedin methanol (10 mL) and to this was added CH3CN (2 mL)and the mixture allowed to evaporate at room temperature. Thedark red crystals of compound 3 were obtained after a period of10 days (40%, m.p 260-262 C). Anal. Calc. for C12H20Cl2N8O2PdS4(613.90): C, 23.46; H, 3.26; N, 18.24. Found: C, 23.20; H, 3.42; N,18.40%. IR bands(KBr, cm1): nu(O-H), 3447m, 3384m; nu(N-H),3308m; nu(C-H), 3081s, 3016w, 2968m, 2938m, 2847s; nu(C-C) +nu(C-N) + delta(C-H), 1581s, 1479s, 1401s, 1284w, 1232w; nu(CS),1119m; 1058m, 951w, 910m, 815m, 740s, 665m, 497m. 1H NMRdata (CDCl3 + dmso-d6 (8:2), delta, ppm, J, Hz): 11.93 (s, NH, 1H,imzSH), 7.25 (s, 2H, C4,5H, imzSH). UV-vis data, DMSO, lambdamax/nm,epsilon/L mol1 cm1: [10-4 M] 441 (2.20 x 103), 340 (1.41 x 104), 265(3.08 x 104). Fluorescence data, DMSO: [10-4 M] (lambdamaxem = 442 nm, lambdamaxex = 342 nm).

Reference： [1]Polyhedron,2017,vol. 127,p. 25 - 35

66
[ 13965-03-2 ]
[ 928-90-5 ]
(S)-methyl 5-amino-4-(4-bromo-1-oxoisoindolin-2-yl)-5-oxopentanoate [ No CAS ]
(S)-methyl 5-amino-4-(4-(6-hydroxyhex-1-yn-1-yl)-1-oxoisoindolin-2-yl)-5-oxopentanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%		A solution of (S)-methyl 5-amino-4-(4-bromo-l-oxoisoindolin-2-yl)-5-oxopentanoate (6.93 g) in DMF (40 mL) and Et3N (40 mL). Nitrogen was bubbled through the mixture for 25 minutes. The mixture was split equally into 4 giving (S)-methyl 5-amino-4-(4-bromo-l- oxoisoindolin-2-yl)-5-oxopentanoate (1.732 g, 4.88 mmol) in DMF (10 mL) and triethylamine (10 mL) per vial. Each vial was treated with hex-5-yn-l-ol (0.80 mL, 7.38 mmol) and copper(l) iodide (0.048 g, 0.252 mmol). Nitrogen was again bubbled through the reaction mixtures for 2 minutes. To each was added bis(triphenylphosphine) palladium(ll) dichloride (0.176 g, 0.251 mmol) and the sealed reaction mixtures were heated at 80C overnight. The reaction mixture was concentrated under reduced pressure and the residue was absorbed onto silica gel. Purification via chromatography (ISCO Combiflash, 80 g column, 60 ml/min, 0-78.4% (3:1 EtOAc / EtOH) / hexanes over 30minutes). The product fractions were collected and concentrated under reduced pressure to yield the title compound (1.72 g, 4.61 mmol, 94%) as an orange oil. LC/MS: RT= 0.68 min, m/z = 373.1.

Reference： [1]Patent: WO2017/46036,2017,A1 .Location in patent: Page/Page column 64; 65

67
[ 13965-03-2 ]
[ 7681-82-5 ]
[ 23523-32-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	In dichloromethane; water; at 20℃; for 8h;	PdCl2 (PPh3) 2 (50 mg, 0.071 mmol),NaI (107 mg, 0.71 mmol),10 mL of dichloromethane,And 10 mL of water were sequentially added to a 50 mL round bottom flask,The reaction was stirred at room temperature for 8 hours and the organic layer was separated,Dried over anhydrous sodium sulfate,Filter concentrate,The crude product was recrystallized from dichloromethane / petroleum ether to give red crystals as PdI2 (PPH3) 2 complex,Yield: 90%.

Reference： [1]Patent: CN106243151,2016,A .Location in patent: Paragraph 0006
[2]Organic Letters,2018,vol. 20,p. 7544 - 7549

68
[ 13965-03-2 ]
(Z)-3-((2-hydroxyphenylimino)methyl)benzene-1,2-diol [ No CAS ]
C₃₁H₂₄NO₃PPd [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	In ethanol; for 12h;Reflux; Inert atmosphere;	General procedure: Nickel (II) and palladium (II) complexes were prepared in twosteps:In first step ONO & ONS tridentate Schiff bases (H2L1 -H2L4) wereprepared by refluxing 2, 3-dihydroxy benzaldehyde/5-chloro-2-hydroxy benzaldehyde with 2-aminophenol/2-aminobenzenethiolin ethanol for 8 h. The orange/yellow colored solid products wereremoved from ethanol by filtration. These crude solids wererecrystallized in ethanol (Scheme 1).In second step complexes were synthesized by refluxing equimolarethanolic solutions of Schiff bases (H2L1 -H2L4) and dichlorobis(triphenylphosphine)nickel/palladium(II) chlorides in 250 mLtwo necked flask under inert conditions for 12 h. The red solidprecipitates appeared on reducing the volume of mother liquorwhich was separated by filtration. The raw solids were recrystallizedin ethanol, dried in air and stored in vacuum dessiccator(Scheme 2).

Reference： [1]Journal of Molecular Structure,2017,vol. 1149,p. 720 - 726

69
[ 13965-03-2 ]
(Z)-3-((2-mercaptophenylimino)methyl)benzene-1,2-diol [ No CAS ]
C₃₁H₂₄NO₂PPdS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	In ethanol; for 12h;Reflux; Inert atmosphere;	General procedure: Nickel (II) and palladium (II) complexes were prepared in twosteps:In first step ONO & ONS tridentate Schiff bases (H2L1 -H2L4) wereprepared by refluxing 2, 3-dihydroxy benzaldehyde/5-chloro-2-hydroxy benzaldehyde with 2-aminophenol/2-aminobenzenethiolin ethanol for 8 h. The orange/yellow colored solid products wereremoved from ethanol by filtration. These crude solids wererecrystallized in ethanol (Scheme 1).In second step complexes were synthesized by refluxing equimolarethanolic solutions of Schiff bases (H2L1 -H2L4) and dichlorobis(triphenylphosphine)nickel/palladium(II) chlorides in 250 mLtwo necked flask under inert conditions for 12 h. The red solidprecipitates appeared on reducing the volume of mother liquorwhich was separated by filtration. The raw solids were recrystallizedin ethanol, dried in air and stored in vacuum dessiccator(Scheme 2).

Reference： [1]Journal of Molecular Structure,2017,vol. 1149,p. 720 - 726

70
[ 13965-03-2 ]
(Z)-4-chloro-2-((2-mercaptophenylimino)methyl)phenol [ No CAS ]
[ 1415126-66-7 ]

Yield	Reaction Conditions	Operation in experiment
78%	In ethanol; for 12h;Reflux; Inert atmosphere;	General procedure: Nickel (II) and palladium (II) complexes were prepared in twosteps:In first step ONO & ONS tridentate Schiff bases (H2L1 -H2L4) wereprepared by refluxing 2, 3-dihydroxy benzaldehyde/5-chloro-2-hydroxy benzaldehyde with 2-aminophenol/2-aminobenzenethiolin ethanol for 8 h. The orange/yellow colored solid products wereremoved from ethanol by filtration. These crude solids wererecrystallized in ethanol (Scheme 1).In second step complexes were synthesized by refluxing equimolarethanolic solutions of Schiff bases (H2L1 -H2L4) and dichlorobis(triphenylphosphine)nickel/palladium(II) chlorides in 250 mLtwo necked flask under inert conditions for 12 h. The red solidprecipitates appeared on reducing the volume of mother liquorwhich was separated by filtration. The raw solids were recrystallizedin ethanol, dried in air and stored in vacuum dessiccator(Scheme 2).

Reference： [1]Journal of Molecular Structure,2017,vol. 1149,p. 720 - 726

71
[ 13965-03-2 ]
[(thf)Zn{B(NDippCH)₂}(μ-Br)]₂ [ No CAS ]
[ 22180-53-6 ]
bromobis(triphenylphosphine)phenylpalladium(II) [ No CAS ]
[ 61111-81-7 ]
Ph₄P[ZnCl₃] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 12 %Spectr. 2: 6%Spectr. 3: 6%Spectr. 4: 15%Spectr.	at 80℃; for 0.5h; Inert atmosphere;

Reference： [1]Campos, Jesús; Nova, Ainara; Kolychev, Eugene L.; Aldridge, Simon [Chemistry - A European Journal, 2017, vol. 23, # 51, p. 12655 - 12667]

72
[ 13965-03-2 ]
[ 3314-32-7 ]
[Pd(Δ-Hbie)(PPh₃)Cl] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium hydroxide; In methanol; dichloromethane; for 48h;Reflux;	A suspension of [Pd(PPh3)2Cl2] (0.0877 g, 0.125 mmol) in CH2Cl2(10 mL) was mixed with Delta-H2bie or Lambda-H2bie (0.037 g, 0.125 mmol)in MeOH containing KOH (0.007 g, 0.125 mmol; 4 mL). The reactionmixture was heated under reflux for 48 h. A yellow complex was obtained, which was filtered off, washed with CH2Cl2, CH3OHand dried in vacuo. 2.3.6.1. For [Pd(Delta-Hbie)(PPh3)Cl]. Yield: 80%. Elemental Anal. Calc.C, 58.54; H, 4.02; Cl, 5.09; N, 8.04; Pd, 15.27 (C34ClH28N4O2PPd).Found: C, 58.50; H, 4.15; Cl, 5.00; N, 8.07; Pd, 15.24%. Conductivitydata (10-3 M in DMF): KM = 8.3 ohm-1 cm2 mol-1.

Reference： [1]Polyhedron,2018,vol. 154,p. 156 - 172

73
[ 13965-03-2 ]
[ 361519-86-0 ]
[Pd(PPh₃)(Λ-H₂bie)Cl] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium hydroxide; In methanol; dichloromethane; for 48h;Reflux;	A suspension of [Pd(PPh3)2Cl2] (0.0877 g, 0.125 mmol) in CH2Cl2(10 mL) was mixed with Delta-H2bie or Lambda-H2bie (0.037 g, 0.125 mmol)in MeOH containing KOH (0.007 g, 0.125 mmol; 4 mL). The reactionmixture was heated under reflux for 48 h. A yellow complex was obtained, which was filtered off, washed with CH2Cl2, CH3OHand dried in vacuo.

Reference： [1]Polyhedron,2018,vol. 154,p. 156 - 172

74
[ 13965-03-2 ]
[ 6410-10-2 ]
C₃₄H₂₅ClN₃O₃PPd [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In ethanol; chloroform for 4h; Reflux;	2.3. Synthesis of Pd(II) 2-(arylazo)naphtholate complexes General procedure: All the new complexes were prepared by the following general procedure. To an ethanolsolution of 1:1 ratio of 2-(p-arylazo)naphtholate ligands (1 mmol, 0.037-0.047 g)was added [Pd(PPh3)2Cl2] (1 mmol, 0.1 g) in CHCl3. The resulting reaction mixture wasthen heated at reflux for 4 h to yield a reddish-purple solution. The solid mass thusobtained was subjected to purification by thin layer chromatography on a silica plate.Chloroform was used as eluent and a reddish purple band separated which wasextracted with 1:1 dichloromethane-chloroform and evaporation of this extract gave[PdCl(PPh3)(L1-5)] as dark pink crystalline solids.

Reference： [1]Munusamy, Sathya; Muniyappan, Premkumar; Galmari, Venkatachalam [Journal of Coordination Chemistry, 2019, vol. 72, # 11, p. 1910 - 1921]

75
[ 13965-03-2 ]
[ 1295605-99-0 ]
chloro-(N1-Phenyl-N3-2-(1-bromo-5-ethoxycarbonylphenyl)-triazenido)-bis(triphenylphosphino)-palladium(II) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%		Triazene 1 (0.342 g, 0.98 mmol) was dissolved in 10 mL of THF. Then 0.5 mL of a 2.04 M solution ofn-butyllithium solution in n-hexane (1.02 mmol) was added dropwise. The color of the solution turnedimmediately dark brown. The reaction solution was stirred for 1.5 h. A suspension ofbis(triphenylphosphane)-dichloro-palladium(II) (0.69 g, 0.98 mmol) in 10 mL of THF was added. Theresulting red-orange mixture was stirred over 2 days and became clear. The solution was filteredthrough a Schlenk frit filled with diatomaceous earth and all volatiles were removed from the filtratein vacuo. The deep red residue was extracted using 10 mL of toluene. The final product was dried invacuo. Yield: 0.515 g of 3 (52%).

Reference： [1]Journal of Organometallic Chemistry,2019,vol. 898

76
[ 13965-03-2 ]
[ 2770-75-4 ]
C₃₉H₃₃N₄P₂PdS₂⁽¹⁺⁾*Cl^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	In dichloromethane for 72h; Reflux;	2.3.4. [Pd(PPh3)2(at)]Cl and [Pt(PPh3)(at)Cl] General procedure: To a suspension of [M(PPh3)2Cl2] (M(II) Pd, Pt) (0.25 mmol) inCH2Cl2 (10 mL), HAT (0.040 g, 0.25 mmol) was added. A pale green(Pd) or brown (Pt) precipitate was obtained after heating underreflux for 72 h. This precipitate was filtered off while hot, washedwith hot CH2Cl2 and air-dried. For [Pd(PPh3)2(at)]Cl: Yield 72%. Anal. Calcd. ForC39ClH33N4P2PdS2: C, 56.73; H, 4.00; Cl, 4.30; N, 6.79; P, 7.50; Pd,12.90; S, 7.76%, Found: C, 56.79; H, 4.1; Cl, 4.30; N, 6.81; S, 7.79; Pd,13.00%. Conductivity data (103M in DMF): Lm 80.31 U1 cm2mol1. IR (cm1); nas(NH2), 3273: ns(NH2), 3180; n(NH), 3076; n(C]N), 1628, 1555; n(C]S), 1170; n(NeCeS), 1406, 1270; n(PdeN),515.1H NMR (500 MHz, DMSO-d6): H (ppm); 7.50 (s, 2H, N (2)H).13C- NMR (500 MHz, DMSO-d6): C (ppm); 154.50, C(2); 173.20, C(4);185.01, C(6). MS (m/z): 789.6 (Calcd. 789.4), 630.8 (Calcd. 630.4),368.0 (Calcd. 368.2).

Reference： [1]Ismail, Amany M.; El Sayed, Shadia A.; Butler, Ian S.; Mostafa, Sahar I. [Journal of Molecular Structure, 2020, vol. 1200]

77
[ 13965-03-2 ]
[ 14901-16-7 ]
C₂₈H₂₃ClN₃PPdS₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	In methanol at 20℃; for 24h;

Reference： [1]Thimma Sambamoorthy, Manikandan; Rengan, Ramesh; Jan Grzegorz, Malecki [Applied Organometallic Chemistry, 2019, vol. 33, # 12]

78
[ 13965-03-2 ]
C₃₀H₃₄N₉PPdS₂ [ No CAS ]
C₃₀H₃₃ClN₉PPd₂S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With lithium hydroxide; In ethanol; at 20℃; for 2h;	To a suspension of complex 1 (0.072 g, 0.1 mmol) in ethanol wasadded solid LiOH (0.008 g, 0.2 mmol) obtaining a solution and thenPdCl2(PPh3)2 (0.07 g, 0.1 mmol) was added. The reaction mixture wasstirred for 2 h at room temperature. The orange solid formed was filtered,washed several times with ethanol, diethyl ether and dried invacuo. The crude product was finally purified by crystallization fromchloroform.Yield (82%), mp > 250 C. Elemental analysis found, C, 42.10; H,3.80; N, 14.70; S, 7.20; C30H33ClN9S2PPd2 requires C, 41.75; H, 3.82; N,14.61; S 7.42%. MS (FAB+ with mNBA matrix) m/z 828 for [M-Cl]+. IR(KBr pellet): /cm-1 3050, 2920 (m, CeH), 1435 (s, PeC); 1587 (w,C]N), 752 (m, C=S-thioamide IV band). 1H NMR (300 MHz,DMSO-d6): delta (ppm) 8.70-7.30 (m, aromatic protons, 15H); 3.32 (s, NMe(a) 12H); 2.55 (s, Me(b) 6H).

Reference： [1]Journal of Inorganic Biochemistry,2020,vol. 203

79
[ 13965-03-2 ]
3,5-diacetyl-1,2,4-triazol bis(N4,N4-dimethylthiosemicarbazone) [ No CAS ]
C₃₀H₃₄N₉PPdS₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With triethylamine; In toluene; at 20℃; for 4h;	This complex was obtained by reaction of PdCl2(PPh3)2 (0.211 g,0,3 mmol), with H3L1 (0.107 g, 0.3 mmol) in toluene, in presence ofEt3N, in 1:1M ratios. The reaction mixture was stirred for 4 h at room temperature. The orange solid formed was filtered, washed severaltimes with hot water, diethyl ether and dried in vacuo. The crude productwas finally purified by crystallization from ethanol.Yield (53%), mp 248 C (d). Elemental analysis found, C, 50.40; H,4.60; N, 17.50; S, 8.60; C30H34N9S2PPd requires C, 49.92; H, 4.71; N,17.47; S 8.87%. MS (FAB+ with mNBA matrix) m/z 721.2 for[M+H]+/[M]+. IR (KBr pellet): /cm-1 3187 (w, NeH); 3050, 2920(m, CeH); 1583 (w, C]N); 1435 (s, PeC); 746 (m, C=S-thioamide IVband). 1H NMR (300 MHz, DMSO-d6): delta (ppm) 12.80 (s, NH, 1H);7.70-7.40 (m, aromatic protons, 15H); 3.33 and 3.08 (s, N-Me(a) 12H);2.39 and 2.29 (s, Me(b) 6H).

Reference： [1]Journal of Inorganic Biochemistry,2020,vol. 203

80
[ 13965-03-2 ]
(E)-N-methyl-2-((4-oxo-4H-chromen-3-yl)methylene)hydrazinecarbothioamide [ No CAS ]
C₃₀H₂₅ClN₃O₂PPdS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	In methanol; at 20℃;	General procedure: A methanolic (30 mL) solution of [PdCl2(PPh3)2] (1 mmol) wasslowly added to chromone TSC (1 mmol) in methanol (30 mL) and themixture was stirred for 10-30 min. The orange colour solution wasevaporated to approximately 3 mL and cooled. Hexane (10 mL) wasthen added whereupon the product complex separated. The orangecolored complex was isolated by filtration, washed with ethanol andhexane, and dried in vacuo. The reaction progress was monitored byTLC.

Reference： [1]Journal of Inorganic Biochemistry,2020,vol. 205

81
[ 13965-03-2 ]
(E)-2-((4-oxo-4H-chromen-3-yl)methylene)-N-phenylhydrazinecarbothioamide [ No CAS ]
C₃₅H₂₇ClN₃O₂PPdS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	In methanol; at 20℃;	General procedure: A methanolic (30 mL) solution of [PdCl2(PPh3)2] (1 mmol) wasslowly added to chromone TSC (1 mmol) in methanol (30 mL) and themixture was stirred for 10-30 min. The orange colour solution wasevaporated to approximately 3 mL and cooled. Hexane (10 mL) wasthen added whereupon the product complex separated. The orangecolored complex was isolated by filtration, washed with ethanol andhexane, and dried in vacuo. The reaction progress was monitored byTLC.

Reference： [1]Journal of Inorganic Biochemistry,2020,vol. 205

82
[ 13965-03-2 ]
N-2-aminomorpholine-N′-benzoylthiourea [ No CAS ]
PdCl(PPh3)(N-2-aminomorpholine-N'-benzoylthioureato-k2N,S) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium hexafluorophosphate; In methanol; at 80℃; for 2h;	General procedure: The complexes were obtained as previously described for similar Pd(II) complexes, from direct reactions of the precursor, [PdCl2(PPh3)2], with the N-alkyl- and N,N-dialkyl-N?-acylthioureas, in methanol solutions [26]. The complexes were separated from the reaction mixtures as yellow crystalline solids. Filtration and further washing with hot water, and with hot hexane, were enough to afford pure compounds, in about 80% yields. Thus, the general procedure for the syntheses of the complexes is described: a solution of [PdCl2(PPh3)2], 1404mg; (2mmol) in 5mL of methanol was added dropwise to a solution of the corresponding N-alkyl- and N,N-dialkyl-N?-acylthiourea (2mmol), dissolved in 30mL of the same solvent, and 368mg (2mmol) of KPF6. The reaction was heated under magnetic stirring at 80C, for 2h. The reaction mixture was left in the refrigerator overnight. The yellow solids obtained were filtered off and washed, successively, with hot water and hot hexane (3×20mL). The obtained compounds are stable in DMSO solutions for at least five days, as was shown by 31P{1H} NMR experiments. Afterwards, the spectra of the complexes were the same when compared with those recorded using fresh solutions. The 1H, 13C{1H} and 31P{1H} NMR data, the elemental analyses, melting point temperature (mp) and molar conductivity (Lambdam, 1.0×10-3 M in CH2Cl2) for the complexes (1-7) are listed below and the other data used for the characterization of the complexes can be found in the text (the multiplicity of signals in the 13C{1H} NMR due to the C-P coupling. 1. [PdCl(PPh3)(N-2-aminomorpholyn-N?-benzoylthioureato-k2N,S) (1).