[ CAS No. 780-69-8 ] {[proInfo.proName]}

Name: 780-69-8|Triethoxy(phenyl)silane|98%
Brand: Ambeed
SKU: A948326
Rating: 99 (29 reviews)

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Cat. No.: {[proInfo.prAm]}

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Quality Control of [ 780-69-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 780-69-8 ]

SDS Specification

Alternatived Products of [ 780-69-8 ]

Product Details of [ 780-69-8 ]

CAS No. :	780-69-8	MDL No. :	MFCD00009065
Formula :	C₁₂H₂₀O₃Si	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JCVQKRGIASEUKR-UHFFFAOYSA-N
M.W :	240.37	Pubchem ID :	13075
Synonyms :

Calculated chemistry of [ 780-69-8 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.5
Num. rotatable bonds :	7
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	67.1
TPSA :	27.69 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.59 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.43
Log Po/w (XLOGP3) :	3.06
Log Po/w (WLOGP) :	1.94
Log Po/w (MLOGP) :	1.26
Log Po/w (SILICOS-IT) :	1.23
Consensus Log Po/w :	2.18

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.07
Solubility :	0.203 mg/ml ; 0.000844 mol/l
Class :	Soluble
Log S (Ali) :	-3.31
Solubility :	0.118 mg/ml ; 0.000492 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.11
Solubility :	0.0189 mg/ml ; 0.0000785 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.95

Safety of [ 780-69-8 ]

Signal Word:	Danger	Class:	3
Precautionary Statements:	P210-P260-P370+P378	UN#:	1993
Hazard Statements:	H225-H373-H412	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 780-69-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 780-69-8 ]
Downstream synthetic route of [ 780-69-8 ]

[ 780-69-8 ] Synthesis Path-Upstream 1~2

1
[ 583-55-1 ]
[ 201230-82-2 ]
[ 780-69-8 ]
[ 13047-06-8 ]

Yield	Reaction Conditions	Operation in experiment
87%	With dichloro bis(acetonitrile) palladium(II); cesium fluoride In 1-methyl-pyrrolidin-2-one at 80℃; for 6 h;	General procedure: A mixture of aryl silane (0.5 mmol), aryl iodines (0.5 mmol), PdCl₂(MeCN)₂(5 molpercent), and CsF (0.5 mmol) was stirred at 80^oC for 6 h in NMP (5 mL) under CO (1atm). Afterwards, 2 mL water was added to the reaction solution and then filtered through a filter paper and the solution was extracted by Et₂O (2 mL) for three times. The organic phase was combined and evaporated under reduced pressure. The residue was purified on a SiO₂ column to afford the desired product (ethyl acetate/hexane).

Reference： [1] Tetrahedron Letters, 2016, vol. 57, # 19, p. 2017 - 2020

2
[ 1021879-02-6 ]
[ 780-69-8 ]
[ 57341-98-7 ]

Reference： [1] Tetrahedron Letters, 2016, vol. 57, # 41, p. 4581 - 4584

[ 780-69-8 ] Synthesis Path-Downstream 1~88

1
[ 4667-38-3 ]
[ 1623-99-0 ]
[ 108-88-3 ]
[ 2553-19-7 ]
[ 780-69-8 ]
[ 1516-80-9 ]

Reference： [1]Takami [1957, vol. 52, p. 179,184][Chem.Abstr., 1958, p. 9982]

2
[ 108-16-7 ]
[ 780-69-8 ]
[ 30718-41-3 ]

Reference： [1]Journal of Organometallic Chemistry,1970,vol. 25,p. 359 - 365

3
[ 3316-09-4 ]
[ 780-69-8 ]
[ 125916-16-7 ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,1989,vol. 42,p. 115 - 122

4
[ 1198-55-6 ]
[ 780-69-8 ]
Potassium; 2,3,4,5-tetrachloro-6-(4,5,6,7-tetrachloro-2-phenyl-benzo[1,3,2]dioxasilol-2-yloxy)-phenolate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With potassium ethoxide In ethanol Heating;

Reference： [1]Evans, Dennis F.; Slawin, Alexandra M. Z.; Williams, David J.; Wong, Chih Y.; Woollins, J. Derek [Journal of the Chemical Society, Dalton Transactions, 1992, # 15, p. 2383 - 2388]

5
[ 3316-09-4 ]
[ 780-69-8 ]
[ 121-44-8 ]
5-Nitro-2-(5-nitro-2-phenyl-benzo[1,3,2]dioxasilol-2-yloxy)-phenol; compound with triethyl-amine [ No CAS ]

Reference： [1]Journal of the Chemical Society, Dalton Transactions,1992,p. 2383 - 2388

6
[ 77-08-7 ]
[ 780-69-8 ]
[ 121-44-8 ]
C₁₀₈H₁₀₀O₁₆Si₄^(4-)*4C₆H₁₅N*4H⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	In tetrahydrofuran for 48h; Heating;

Reference： [1]Small, James H.; McCord, Dianne J.; Greaves, John; Shea [Journal of the American Chemical Society, 1995, vol. 117, # 46, p. 11588 - 11589]

7
[ 74-96-4 ]
[ 78-10-4 ]
[ 108-90-7 ]
[ 92-52-4 ]
[ 1048-08-4 ]
[ 2553-19-7 ]
[ 780-69-8 ]
[ 1516-80-9 ]
[ 71-43-2 ]

Yield	Reaction Conditions	Operation in experiment
	With methyl bottoms various compositions of methyl bottoms, various supply rates;

Reference： [1]Klokov [Russian Journal of Applied Chemistry, 1998, vol. 71, # 3, p. 476 - 478]

8
[ 402-43-7 ]
[ 780-69-8 ]
[ 398-36-7 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium hydroxide In water at 120℃; for 3h;
87%	With N,N-bis(indolin-1-yl)ethane-1,2-diimine; tetrabutyl ammonium fluoride In tetrahydrofuran; toluene at 80℃; for 3h;
81%	With tetrabutyl ammonium fluoride; palladium diacetate; di(1-adamantyl)-N-butylphosphine hydroiodide at 80℃; for 24h; Inert atmosphere; Sealed tube; Green chemistry;

94 % Chromat.

With sodium hydroxide In 1,4-dioxane at 80℃; for 4h;

Reference： [1]Chen, Shao-Nung; Wu, Wei-Yi; Tsai, Fu-Yu [Tetrahedron, 2008, vol. 64, # 35, p. 8164 - 8168]
[2]Mino, Takashi; Shirae, Yoshiaki; Saito, Takeshi; Sakamoto, Masami; Fujita, Tsutomu [Journal of Organic Chemistry, 2006, vol. 71, # 25, p. 9499 - 9502]
[3]Gevorgyan, Ashot; Hopmann, Kathrin H.; Bayer, Annette [Green Chemistry, 2021, vol. 23, # 18, p. 7219 - 7227]
[4]Murata; Shimazaki; Watanabe; Masuda [Synthesis, 2001, # 15, p. 2231 - 2233]

9
[ 455-19-6 ]
[ 780-69-8 ]
[ 395-23-3 ]

Reference： [1]Synthesis,2002,p. 717 - 719

10
[ 780-69-8 ]
[ 123-11-5 ]
[ 720-44-5 ]

Yield	Reaction Conditions	Operation in experiment
70%	With sodium hydroxide; cyclo-octa-1,5-diene In 1,4-dioxane at 90℃; for 16h;

Reference： [1]Murata, Miki; Shimazaki, Ryuta; Ishikura, Masanori; Watanabe, Shinji; Masuda, Yuzuru [Synthesis, 2002, # 6, p. 717 - 719]

11
[ 780-69-8 ]
[ 185847-84-1 ]
[ 335266-05-2 ]

Reference： [1]Chemical Communications,2007,p. 710 - 712

12
[ 78-10-4 ]
[ 2553-19-7 ]
[ 780-69-8 ]
[ 1516-80-9 ]

Yield	Reaction Conditions	Operation in experiment
35-40	With bromobenzene; magnesium In toluene byproducts: diphenyl; at 100°C;;
35-40	With C₆H₅Br; Mg In toluene byproducts: diphenyl; at 100°C;;

Reference： [1]Topchiev, A. V.; Nametkin, N. S. [Doklady Akademii Nauk SSSR, 1951, vol. 80, p. 897 - 898][C. A., 1952, p. 7534]
[2][Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 76, page 212 - 214]

13
[ 106-39-8 ]
[ 780-69-8 ]
[ 2051-62-9 ]

Yield	Reaction Conditions	Operation in experiment
94%	Stage #1: triethoxyphenylsilane With tetrabutyl ammonium fluoride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: bromochlorobenzene With [Pd{C₆H₂-(CH₂CH₂NH₂)-(OMe)2-3,4}Br(PPh₃)] In N,N-dimethyl-formamide at 100℃; for 0.0333333h; Microwave irradiation;	General procedure for the Hiyama reaction of aryl halides General procedure: A mixture of TBAF·3H2O (1.2 mmol) and triethoxy(phenyl)silane (1.2 mmol) in DMF (2 ml) was stirred at room temperature for 1 h, then the aryl halide (1 mmol) and ortho-palladated catalyst (0.4 mol %) were added and the mixture placed into a Milestone microwave reactor. Initially the microwave irradiation was set at 600 W, and the temperature was ramped from room temperature to the desired temperature (100 °C). Once this was reached, the mixture was held at this temperature until the reaction was complete. The mixture was stirred continuously and monitored by both TLC and GC. After the reaction was complete, the mixture was cooled to room temperature, and was extracted with Et2O (30 ml). The organic phase was washed with H2O (30 ml), and dried over MgSO4, filtered, and concentrated under reduced pressure using a rotary evaporator. The residue was purified by silica gel column chromatography.
94%	Stage #1: triethoxyphenylsilane With tetrabutyl ammonium fluoride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: bromochlorobenzene With [Pd{C₆H₂(CH₂CH₂NH₂)-(OMe)₂-2,3}(μ-Br)]₂ In N,N-dimethyl-formamide at 100℃; for 0.0833333h; Microwave irradiation;
94%	With sodium hydroxide In water at 80℃; for 3h;	2.8 General Procedure for Hiyama Cross-CouplingReaction General procedure: To a stirring mixture of aryl halide (1 mmol), triethoxyphenylsilane(1.2 mmol) and NaOH (2 mmol) in H2O(4 mL),γ-Fe2O3-Pd-NHC-n-butyl-SO3Na (0.08 or 0.16 mol% based on Pd) was added. The resulting mixture was stirred at 80 °Cfor an appropriate time indicated by TLC monitoring. Aftercooling the reaction to room temperature, the catalyst wasseparated by an external magnet and washed with EtOAc.The product was extracted from the aqueous phase usingEtOAc (3 × 5 mL). After drying the combined organic layersover anhydrous Na2SO4,the solvent was evaporated togive the crude product. Purification of the crude product bycolumn chromatography on silica gel eluted with n-hexane:EtOAc = 30:1 produced the pure products (1-6).

92%	Stage #1: triethoxyphenylsilane With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 1h; Stage #2: bromochlorobenzene With [Pd{C₆H₄(CH₂N(CH₂Ph)₂)}(μ-Br)]₂ In N,N-dimethyl-formamide at 90℃; for 0.0333333h; Microwave irradiation; chemoselective reaction;
90%	With triethylamine In N,N-dimethyl-formamide at 90℃; for 3h;
88%	With sodium hydroxide In water at 120℃; for 36h;
87%	With sodium hydroxide In water at 90℃; for 3h; Green chemistry;
81%	With tetrabutyl ammonium fluoride; acetic acid In toluene at 100℃; for 24h;
99 %Chromat.	With [palladium(II) 1-(4-N,N’,N’’-trimethylbutylammonium)-4-(2-pyridyl)-1H-1,2,3-triazoledichloride]chloride; tetrabutylammomium bromide; sodium hydroxide In water at 120℃; for 6h;

Reference： [1]Location in patent: experimental part Hajipour, Abdol Reza; Rafiee, Fatemeh [Tetrahedron Letters, 2012, vol. 53, # 35, p. 4661 - 4664]
[2]Hajipour, Abdol R.; Rafiee, Fatemeh [Applied Organometallic Chemistry, 2013, vol. 27, # 7, p. 412 - 418]
[3]Chahkamali, Farhad Omarzehi; Sansano, José Miguel; Sobhani, Sara [Catalysis Letters, 2021]
[4]Location in patent: experimental part Hajipour, Abdol R.; Rafiee, Fatemeh [Applied Organometallic Chemistry, 2012, vol. 26, # 2, p. 51 - 55]
[5]Farrokhi, Alireza; Rouzifar, Majid; Sansano, José Miguel; Sobhani, Sara [New Journal of Chemistry, 2021, vol. 45, # 42, p. 19963 - 19976]
[6]Chen, Shao-Nung; Wu, Wei-Yi; Tsai, Fu-Yu [Tetrahedron, 2008, vol. 64, # 35, p. 8164 - 8168]
[7]Sobhani, Sara; Hosseini Moghadam, Hadis; Skibsted, Jørgen; Sansano, José Miguel [Green Chemistry, 2020, vol. 22, # 4, p. 1353 - 1365]
[8]Huang, Shao-Hsien; Liu, Chun-Hsia; Yang, Chia-Min [Green Chemistry, 2014, vol. 16, # 5, p. 2706 - 2712]
[9]Kong, Fanzhen; Zhou, Chunshan; Wang, Jinyun; Yu, Zhangyu; Wang, Ruihu [ChemPlusChem, 2013, vol. 78, # 6, p. 536 - 545]

14
[ 1564-64-3 ]
[ 780-69-8 ]
[ 602-55-1 ]

Yield	Reaction Conditions	Operation in experiment
88%	With sodium hydroxide In water at 120℃; for 24h;

Reference： [1]Chen, Shao-Nung; Wu, Wei-Yi; Tsai, Fu-Yu [Tetrahedron, 2008, vol. 64, # 35, p. 8164 - 8168]

15
[ 2142-69-0 ]
[ 780-69-8 ]
[ 2142-66-7 ]

Yield	Reaction Conditions	Operation in experiment
68%		General procedure: A mixture of TBAF·3H2O (1.2 mmol) and triethoxy(phenyl)silane (1.2 mmol) in DMF (2 ml) was stirred at room temperature for 1 h, then the aryl halide (1 mmol) and ortho-palladated catalyst (0.4 mol %) were added and the mixture placed into a Milestone microwave reactor. Initially the microwave irradiation was set at 600 W, and the temperature was ramped from room temperature to the desired temperature (100 C). Once this was reached, the mixture was held at this temperature until the reaction was complete. The mixture was stirred continuously and monitored by both TLC and GC. After the reaction was complete, the mixture was cooled to room temperature, and was extracted with Et2O (30 ml). The organic phase was washed with H2O (30 ml), and dried over MgSO4, filtered, and concentrated under reduced pressure using a rotary evaporator. The residue was purified by silica gel column chromatography.

Reference： [1]Applied Organometallic Chemistry,2014,vol. 28,p. 217 - 220
[2]Applied Organometallic Chemistry,2012,vol. 26,p. 51 - 55
[3]Tetrahedron Letters,2012,vol. 53,p. 4661 - 4664
[4]Catalysis Communications,2018,vol. 103,p. 92 - 95
[5]Tetrahedron,2008,vol. 64,p. 8164 - 8168
[6]Tetrahedron,2010,vol. 66,p. 9502 - 9507

16
[ 780-69-8 ]
[ 345958-72-7 ]
[ 398-36-7 ]

Yield	Reaction Conditions	Operation in experiment
81%	With dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl; tetrabutyl ammonium fluoride; palladium diacetate In tetrahydrofuran at 80℃; Inert atmosphere;

Reference： [1]Zhang, Liang; Wu, Jie [Journal of the American Chemical Society, 2008, vol. 130, # 37, p. 12250 - 12251]

17
[ 1092513-18-2 ]
[ 780-69-8 ]
[ 612-95-3 ]

Reference： [1]Organic Letters,2009,vol. 11,p. 317 - 320

18
[ 17180-93-7 ]
[ 780-69-8 ]
[ 3438-48-0 ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 9046 - 9048

19
[ 18368-76-8 ]
[ 780-69-8 ]
[ 10273-90-2 ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 9046 - 9048

20
[ 7283-96-7 ]
[ 780-69-8 ]
[ 19163-21-4 ]

Yield	Reaction Conditions	Operation in experiment
92%	With Pd((CH₃)2C₆H₃NC(CH₃)CHC(CH₃)NC₆H₃(CH₃)2)(CH₃)(P(CH₂CH₃)3); tetrabutylammomium bromide; sodium hydroxide In water at 60℃; for 8h; Inert atmosphere;

Reference： [1]Lee, Dong-Hwan; Jung, Ji-Young; Jin, Myung-Jong [Chemical Communications, 2010, vol. 46, # 47, p. 9046 - 9048]

21
[ 87-65-0 ]
[ 780-69-8 ]
[ 2432-11-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	With Pd((CH₃)2C₆H₃NC(CH₃)CHC(CH₃)NC₆H₃(CH₃)2)(CH₃)(P(CH₂CH₃)3); tetrabutylammomium bromide; sodium hydroxide In water at 80℃; for 10h; Inert atmosphere;

Reference： [1]Lee, Dong-Hwan; Jung, Ji-Young; Jin, Myung-Jong [Chemical Communications, 2010, vol. 46, # 47, p. 9046 - 9048]

22
[ 780-69-8 ]
[ 95-50-1 ]
[ 84-15-1 ]

Yield	Reaction Conditions	Operation in experiment
91%	With Pd((CH₃)2C₆H₃NC(CH₃)CHC(CH₃)NC₆H₃(CH₃)2)(CH₃)(P(CH₂CH₃)3); tetrabutylammomium bromide; sodium hydroxide In water at 80℃; for 10h; Inert atmosphere;

Reference： [1]Lee, Dong-Hwan; Jung, Ji-Young; Jin, Myung-Jong [Chemical Communications, 2010, vol. 46, # 47, p. 9046 - 9048]

23
[ 636-98-6 ]
[ 780-69-8 ]
[ 92-93-3 ]

Yield	Reaction Conditions	Operation in experiment
96%		General procedure: A mixture of TBAF·3H2O (1.2 mmol) and triethoxy(phenyl)silane (1.2 mmol) in DMF (2 ml) was stirred at room temperature for 1 h, then the aryl halide (1 mmol) and ortho-palladated catalyst (0.4 mol %) were added and the mixture placed into a Milestone microwave reactor. Initially the microwave irradiation was set at 600 W, and the temperature was ramped from room temperature to the desired temperature (100 C). Once this was reached, the mixture was held at this temperature until the reaction was complete. The mixture was stirred continuously and monitored by both TLC and GC. After the reaction was complete, the mixture was cooled to room temperature, and was extracted with Et2O (30 ml). The organic phase was washed with H2O (30 ml), and dried over MgSO4, filtered, and concentrated under reduced pressure using a rotary evaporator. The residue was purified by silica gel column chromatography.

Reference： [1]Applied Organometallic Chemistry,2014,vol. 28,p. 217 - 220
[2]Tetrahedron Letters,2012,vol. 53,p. 4661 - 4664
[3]Applied Organometallic Chemistry,2012,vol. 26,p. 51 - 55
[4]Chemistry Letters,2011,vol. 40,p. 910 - 912
[5]Synthesis,2013,vol. 45,p. 40 - 44

24
[ 623-00-7 ]
[ 780-69-8 ]
[ 2920-38-9 ]

Yield	Reaction Conditions	Operation in experiment
96%	Stage #1: triethoxyphenylsilane With tetrabutyl ammonium fluoride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 4-bromobenzenecarbonitrile With [Pd{C₆H₂(CH₂CH₂NH₂)-(OMe)₂-2,3}(μ-Br)]₂ In N,N-dimethyl-formamide at 100℃; for 0.0666667h; Microwave irradiation;
95%	Stage #1: triethoxyphenylsilane With cesium fluoride In 1-methyl-pyrrolidin-2-one at 20℃; for 1h; Stage #2: 4-bromobenzenecarbonitrile With (1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane)₂Pd₂Cl₆ In 1-methyl-pyrrolidin-2-one at 20 - 100℃; for 0.0666667h; Microwave irradiation;
94%	Stage #1: triethoxyphenylsilane With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 1h; Stage #2: 4-bromobenzenecarbonitrile With [Pd{C₆H₄(CH₂N(CH₂Ph)₂)}(μ-Br)]₂ In N,N-dimethyl-formamide at 90℃; for 0.0833333h; Microwave irradiation;

93%	Stage #1: triethoxyphenylsilane With tetrabutyl ammonium fluoride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 4-bromobenzenecarbonitrile With [Pd{C₆H₂-(CH₂CH₂NH₂)-(OMe)2-3,4}Br(PPh₃)] In N,N-dimethyl-formamide at 100℃; for 0.0666667h; Microwave irradiation;	General procedure for the Hiyama reaction of aryl halides General procedure: A mixture of TBAF·3H2O (1.2 mmol) and triethoxy(phenyl)silane (1.2 mmol) in DMF (2 ml) was stirred at room temperature for 1 h, then the aryl halide (1 mmol) and ortho-palladated catalyst (0.4 mol %) were added and the mixture placed into a Milestone microwave reactor. Initially the microwave irradiation was set at 600 W, and the temperature was ramped from room temperature to the desired temperature (100 °C). Once this was reached, the mixture was held at this temperature until the reaction was complete. The mixture was stirred continuously and monitored by both TLC and GC. After the reaction was complete, the mixture was cooled to room temperature, and was extracted with Et2O (30 ml). The organic phase was washed with H2O (30 ml), and dried over MgSO4, filtered, and concentrated under reduced pressure using a rotary evaporator. The residue was purified by silica gel column chromatography.
92%	With sodium hydroxide In water at 80℃; for 4.5h;	2.8 General Procedure for Hiyama Cross-CouplingReaction General procedure: To a stirring mixture of aryl halide (1 mmol), triethoxyphenylsilane(1.2 mmol) and NaOH (2 mmol) in H2O(4 mL),γ-Fe2O3-Pd-NHC-n-butyl-SO3Na (0.08 or 0.16 mol% based on Pd) was added. The resulting mixture was stirred at 80 °Cfor an appropriate time indicated by TLC monitoring. Aftercooling the reaction to room temperature, the catalyst wasseparated by an external magnet and washed with EtOAc.The product was extracted from the aqueous phase usingEtOAc (3 × 5 mL). After drying the combined organic layersover anhydrous Na2SO4,the solvent was evaporated togive the crude product. Purification of the crude product bycolumn chromatography on silica gel eluted with n-hexane:EtOAc = 30:1 produced the pure products (1-6).
90%	With sodium hydroxide In water at 90℃; for 2.5h; Green chemistry;
89%	With sodium hydroxide In ethanol at 25℃; for 3h; Irradiation; Sealed tube; Green chemistry;
87%	With triethylamine In N,N-dimethyl-formamide at 90℃; for 4h;
86%	With tetrabutyl ammonium fluoride In toluene at 90℃; for 9h;
85%	With palladium 10% on activated carbon; tetrabutyl ammonium fluoride; water; P(p-C₆H₄F)3 In toluene at 120℃; for 12h; Inert atmosphere;
85%	With palladium 10% on activated carbon; tetrabutyl ammonium fluoride; P(p-C₆H₄F)3 In water; toluene at 120℃; for 12h; Inert atmosphere;
71%	With tetrabutyl ammonium fluoride; acetic acid In toluene at 100℃; for 24h;

Reference： [1]Hajipour, Abdol R.; Rafiee, Fatemeh [Applied Organometallic Chemistry, 2013, vol. 27, # 7, p. 412 - 418]
[2]Hajipour, Abdol R.; Rafiee, Fatemeh; Najafi, Narges [Applied Organometallic Chemistry, 2014, vol. 28, # 4, p. 217 - 220]
[3]Location in patent: experimental part Hajipour, Abdol R.; Rafiee, Fatemeh [Applied Organometallic Chemistry, 2012, vol. 26, # 2, p. 51 - 55]
[4]Location in patent: experimental part Hajipour, Abdol Reza; Rafiee, Fatemeh [Tetrahedron Letters, 2012, vol. 53, # 35, p. 4661 - 4664]
[5]Chahkamali, Farhad Omarzehi; Sansano, José Miguel; Sobhani, Sara [Catalysis Letters, 2021]
[6]Sobhani, Sara; Hosseini Moghadam, Hadis; Skibsted, Jørgen; Sansano, José Miguel [Green Chemistry, 2020, vol. 22, # 4, p. 1353 - 1365]
[7]Jahanshahi, Roya; Khazaee, Asma; Sobhani, Sara; Sansano, José Miguel [New Journal of Chemistry, 2020, vol. 44, # 27, p. 11513 - 11526]
[8]Farrokhi, Alireza; Rouzifar, Majid; Sansano, José Miguel; Sobhani, Sara [New Journal of Chemistry, 2021, vol. 45, # 42, p. 19963 - 19976]
[9]Movassagh, Barahman; Parvis, Fatemeh S.; Navidi, Mozhgan [Applied Organometallic Chemistry, 2015, vol. 29, # 1, p. 40 - 44]
[10]Yanase, Takayoshi; Mori, Shigeki; Monguchi, Yasunari; Sajiki, Hironao [Chemistry Letters, 2011, vol. 40, # 9, p. 910 - 912]
[11]Monguchi, Yasunari; Yanase, Takayoshi; Mori, Shigeki; Sajiki, Hironao [Synthesis, 2013, vol. 45, # 1, p. 40 - 44]
[12]Huang, Shao-Hsien; Liu, Chun-Hsia; Yang, Chia-Min [Green Chemistry, 2014, vol. 16, # 5, p. 2706 - 2712]

25
[ 780-69-8 ]
[ 100-00-5 ]
[ 92-93-3 ]

Yield	Reaction Conditions	Operation in experiment
70%		General procedure: A mixture of TBAF·3H2O (1.2 mmol) and triethoxy(phenyl)silane (1.2 mmol) in DMF (2 ml) was stirred at room temperature for 1 h, then the aryl halide (1 mmol) and ortho-palladated catalyst (0.4 mol %) were added and the mixture placed into a Milestone microwave reactor. Initially the microwave irradiation was set at 600 W, and the temperature was ramped from room temperature to the desired temperature (100 C). Once this was reached, the mixture was held at this temperature until the reaction was complete. The mixture was stirred continuously and monitored by both TLC and GC. After the reaction was complete, the mixture was cooled to room temperature, and was extracted with Et2O (30 ml). The organic phase was washed with H2O (30 ml), and dried over MgSO4, filtered, and concentrated under reduced pressure using a rotary evaporator. The residue was purified by silica gel column chromatography.

Reference： [1]Green Chemistry,2020,vol. 22,p. 1353 - 1365
[2]Dalton Transactions,2012,vol. 41,p. 12031 - 12037
[3]Catalysis Communications,2018,vol. 103,p. 92 - 95
[4]Applied Organometallic Chemistry,2018,vol. 32
[5]New Journal of Chemistry,2020,vol. 44,p. 11513 - 11526
[6]Applied Organometallic Chemistry,2014,vol. 28,p. 217 - 220
[7]Tetrahedron Letters,2012,vol. 53,p. 4661 - 4664
[8]Applied Organometallic Chemistry,2012,vol. 26,p. 51 - 55
[9]Chemistry Letters,2011,vol. 40,p. 910 - 912
[10]Synthesis,2013,vol. 45,p. 40 - 44
[11]Green Chemistry,2014,vol. 16,p. 2706 - 2712

26
[ 108-37-2 ]
[ 780-69-8 ]
[ 2051-61-8 ]

Yield	Reaction Conditions	Operation in experiment
92%		General procedure: A mixture of TBAF·3H2O (1.2 mmol) and triethoxy(phenyl)silane (1.2 mmol) in DMF (2 ml) was stirred at room temperature for 1 h, then the aryl halide (1 mmol) and ortho-palladated catalyst (0.4 mol %) were added and the mixture placed into a Milestone microwave reactor. Initially the microwave irradiation was set at 600 W, and the temperature was ramped from room temperature to the desired temperature (100 C). Once this was reached, the mixture was held at this temperature until the reaction was complete. The mixture was stirred continuously and monitored by both TLC and GC. After the reaction was complete, the mixture was cooled to room temperature, and was extracted with Et2O (30 ml). The organic phase was washed with H2O (30 ml), and dried over MgSO4, filtered, and concentrated under reduced pressure using a rotary evaporator. The residue was purified by silica gel column chromatography.

Reference： [1]Applied Organometallic Chemistry,2012,vol. 26,p. 51 - 55
[2]Applied Organometallic Chemistry,2014,vol. 28,p. 217 - 220
[3]Tetrahedron Letters,2012,vol. 53,p. 4661 - 4664
[4]Applied Organometallic Chemistry,2013,vol. 27,p. 412 - 418

27
[ 6136-66-9 ]
[ 780-69-8 ]
[ 2128-93-0 ]

Reference： [1]Applied Organometallic Chemistry,2012,vol. 26,p. 51 - 55
[2]Applied Organometallic Chemistry,2013,vol. 27,p. 412 - 418

28
[ 780-69-8 ]
[ 2142-63-4 ]
[ 3112-01-4 ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: triethoxyphenylsilane With cesium fluoride In 1-methyl-pyrrolidin-2-one at 20℃; for 1h; Stage #2: 1-(3-Bromophenyl)ethanone With (1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane)₂Pd₂Cl₆ In 1-methyl-pyrrolidin-2-one at 20 - 100℃; for 0.166667h; Microwave irradiation;
83%	Stage #1: triethoxyphenylsilane With tetrabutyl ammonium fluoride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 1-(3-Bromophenyl)ethanone With [Pd{C₆H₂-(CH₂CH₂NH₂)-(OMe)2-3,4}Br(PPh₃)] In N,N-dimethyl-formamide at 100℃; for 0.166667h; Microwave irradiation;	General procedure for the Hiyama reaction of aryl halides General procedure: A mixture of TBAF·3H2O (1.2 mmol) and triethoxy(phenyl)silane (1.2 mmol) in DMF (2 ml) was stirred at room temperature for 1 h, then the aryl halide (1 mmol) and ortho-palladated catalyst (0.4 mol %) were added and the mixture placed into a Milestone microwave reactor. Initially the microwave irradiation was set at 600 W, and the temperature was ramped from room temperature to the desired temperature (100 °C). Once this was reached, the mixture was held at this temperature until the reaction was complete. The mixture was stirred continuously and monitored by both TLC and GC. After the reaction was complete, the mixture was cooled to room temperature, and was extracted with Et2O (30 ml). The organic phase was washed with H2O (30 ml), and dried over MgSO4, filtered, and concentrated under reduced pressure using a rotary evaporator. The residue was purified by silica gel column chromatography.
78%	Stage #1: triethoxyphenylsilane With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 1h; Stage #2: 1-(3-Bromophenyl)ethanone With [Pd{C₆H₄(CH₂N(CH₂Ph)₂)}(μ-Br)]₂ In N,N-dimethyl-formamide at 90℃; for 0.133333h; Microwave irradiation;

49 %Spectr.

With palladium 10% on activated carbon; tetrabutyl ammonium fluoride; P(p-C₆H₄F)3 In water; toluene at 120℃; for 24h; Inert atmosphere;

Reference： [1]Hajipour, Abdol R.; Rafiee, Fatemeh; Najafi, Narges [Applied Organometallic Chemistry, 2014, vol. 28, # 4, p. 217 - 220]
[2]Location in patent: experimental part Hajipour, Abdol Reza; Rafiee, Fatemeh [Tetrahedron Letters, 2012, vol. 53, # 35, p. 4661 - 4664]
[3]Location in patent: experimental part Hajipour, Abdol R.; Rafiee, Fatemeh [Applied Organometallic Chemistry, 2012, vol. 26, # 2, p. 51 - 55]
[4]Monguchi, Yasunari; Yanase, Takayoshi; Mori, Shigeki; Sajiki, Hironao [Synthesis, 2013, vol. 45, # 1, p. 40 - 44]

29
[ 645-00-1 ]
[ 780-69-8 ]
[ 2113-58-8 ]

Yield	Reaction Conditions	Operation in experiment
92%		General procedure: A mixture of TBAF·3H2O (1.2 mmol) and triethoxy(phenyl)silane (1.2 mmol) in DMF (2 ml) was stirred at room temperature for 1 h, then the aryl halide (1 mmol) and ortho-palladated catalyst (0.4 mol %) were added and the mixture placed into a Milestone microwave reactor. Initially the microwave irradiation was set at 600 W, and the temperature was ramped from room temperature to the desired temperature (100 C). Once this was reached, the mixture was held at this temperature until the reaction was complete. The mixture was stirred continuously and monitored by both TLC and GC. After the reaction was complete, the mixture was cooled to room temperature, and was extracted with Et2O (30 ml). The organic phase was washed with H2O (30 ml), and dried over MgSO4, filtered, and concentrated under reduced pressure using a rotary evaporator. The residue was purified by silica gel column chromatography.

Reference： [1]Applied Organometallic Chemistry,2014,vol. 28,p. 217 - 220
[2]Tetrahedron Letters,2012,vol. 53,p. 4661 - 4664

30
[ 623-03-0 ]
[ 780-69-8 ]
[ 2920-38-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium hydroxide In water at 80℃; for 6h;	2.8 General Procedure for Hiyama Cross-CouplingReaction General procedure: To a stirring mixture of aryl halide (1 mmol), triethoxyphenylsilane(1.2 mmol) and NaOH (2 mmol) in H2O(4 mL),γ-Fe2O3-Pd-NHC-n-butyl-SO3Na (0.08 or 0.16 mol% based on Pd) was added. The resulting mixture was stirred at 80 °Cfor an appropriate time indicated by TLC monitoring. Aftercooling the reaction to room temperature, the catalyst wasseparated by an external magnet and washed with EtOAc.The product was extracted from the aqueous phase usingEtOAc (3 × 5 mL). After drying the combined organic layersover anhydrous Na2SO4,the solvent was evaporated togive the crude product. Purification of the crude product bycolumn chromatography on silica gel eluted with n-hexane:EtOAc = 30:1 produced the pure products (1-6).
89%	With C₅₈H₇₈Cl₄N₆Pd₂; tetrabutyl ammonium fluoride In toluene at 120℃; for 5h;
85%	With triethylamine In N,N-dimethyl-formamide at 90℃; for 4h;

80%	With sodium hydroxide In water at 90℃; for 3.5h; Green chemistry;
80%	With sodium hydroxide In ethanol at 25℃; for 4.5h; Irradiation; Sealed tube; Green chemistry;

Reference： [1]Chahkamali, Farhad Omarzehi; Sansano, José Miguel; Sobhani, Sara [Catalysis Letters, 2021]
[2]Yang, Jin; Wang, Lei [Dalton Transactions, 2012, vol. 41, # 39, p. 12031 - 12037]
[3]Farrokhi, Alireza; Rouzifar, Majid; Sansano, José Miguel; Sobhani, Sara [New Journal of Chemistry, 2021, vol. 45, # 42, p. 19963 - 19976]
[4]Sobhani, Sara; Hosseini Moghadam, Hadis; Skibsted, Jørgen; Sansano, José Miguel [Green Chemistry, 2020, vol. 22, # 4, p. 1353 - 1365]
[5]Jahanshahi, Roya; Khazaee, Asma; Sobhani, Sara; Sansano, José Miguel [New Journal of Chemistry, 2020, vol. 44, # 27, p. 11513 - 11526]

31
[ 780-69-8 ]
[ 15898-38-1 ]
[ 643-93-6 ]

Yield	Reaction Conditions	Operation in experiment
89%	With tetrabutyl ammonium fluoride; palladium dichloride In tetrahydrofuran at 70℃; for 3h;

Reference： [1]Cheng, Kai; Hu, Sai; Zhao, Baoli; Zhang, Xian-Man; Qi, Chenze [Journal of Organic Chemistry, 2013, vol. 78, # 10, p. 5022 - 5025]

32
[ 780-69-8 ]
[ 15898-46-1 ]
[ 2113-58-8 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 5022 - 5025

33
[ 935447-39-5 ]
[ 780-69-8 ]
[ 2367-22-8 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 5022 - 5025

34
[ 780-69-8 ]
[ 15946-36-8 ]
[ 2051-60-7 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 5022 - 5025

35
[ 780-69-8 ]
[ 63735-42-2 ]
[ 612-94-2 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 5022 - 5025

36
[ 780-69-8 ]
[ 99-09-2 ]
[ 2113-58-8 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: The concentration of0.25mol aniline was dissolved in the mixture of 63 ml HCl and 63 ml water in600 ml beaker. After cooled to 0-5 oC with stirring, anilinehydrochloride crystallization. Aqueous solution of sodium nitrite (18gdissolved in 40 ml water) was added into beaker dropwise with stirring, keepingthe temperature under 5 oC. 40 g of sodium tetrafluoroboratesolution dissolved in 80 ml water was added to the diazonium salt solution, andthen continue to stir for 10 minutes. The solid was immediately washed by 10 ml5 % solution of sodium tetrafluoroborate for three times after filtered, andthen washed by 15 ml methanol twice to afford diazonium salt.A mixture of arenediazonium tetrafluoroborate salt(0.5 mmol), Pd(OAc)2 (5 mol%), TBAF (0.5 mmol) and aryl silanes (0.6mmol) was stirred in water (1 mL) at room termperature for 6 h. Afterwards, thereaction solution was filtered through a filter paper and the solution wasextracted by Et2O (1 mL) for three times. The organic phase wascombined and evaporated under reduced pressure. The residue was purified on aSiO2 column to afford the desired product.

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 6211 - 6214

37
[ 624-31-7 ]
[ 780-69-8 ]
[ 92-52-4 ]
[ 613-33-2 ]
[ 644-08-6 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 5378 - 5381

38
[ 625-95-6 ]
[ 780-69-8 ]
[ 643-93-6 ]

Yield	Reaction Conditions	Operation in experiment
69%	With bis-triphenylphosphine-palladium(II) chloride; tetrabutylphosphonium 4-ethoxyvalerate; tetrabutyl ammonium fluoride at 130℃; for 24h; Green chemistry;	General procedure for Hiyama coupling reactions General procedure: In a 4 mL screw-cap vial, 0.5 mmol of the corresponding iodoarene compounds, 1.5 eq of the corresponding silane, 1.5 eq of tetrabutylammonium fluoride (TBAF), 0.01 eq PdCl2(PPh3)2, and 0.8 mL of tetrabutylphosphonium 4-ethoxyvalerate ([TBP][4EtOV]) ionic liquid were mixed and stirred at 130 °C for 24 h. After cooling, the mixture was partitioned between 5 mL of 1 M HCl and 5 mL of pentane. The aqueous phase was extracted subsequently with 3 * 5 mL of pentane. The combined organic phase was washed with brine, dried over MgSO4, and filtered, and the solvent was evaporated under reduced pressure (ca. 1.333 kPa). The residue was purified by chromatography on silica gel (Merck Silicagel 60 (0.063-0.200 mm) for column chromatography (70-230 mesh ASTM)) eluted with n-pentane:EtOAc. The detailed experimental procedure, as well as the characterization of isolated compounds are provided in the Supporting Information.
58%	With copper(l) iodide; cesium fluoride; N,N-dimethyl-2-(diphenylphosphino)aniline In N,N-dimethyl-formamide at 120℃; for 24h; Inert atmosphere;

Reference： [1]Orha, László; Papp, Ábrahám; Tukacs, József M.; Kollár, László; Mika, László T. [Chemical Papers, 2020, vol. 74, # 12, p. 4593 - 4598]
[2]Gurung, Santosh K.; Thapa, Surendra; Vangala, Adarsh S.; Giri, Ramesh [Organic Letters, 2013, vol. 15, # 20, p. 5378 - 5381]

39
[ 625-95-6 ]
[ 780-69-8 ]
[ 612-75-9 ]
[ 643-93-6 ]

Yield	Reaction Conditions	Operation in experiment
	With copper(l) iodide; cesium fluoride In N,N-dimethyl-formamide at 120℃; for 24h; Inert atmosphere;

Reference： [1]Gurung, Santosh K.; Thapa, Surendra; Vangala, Adarsh S.; Giri, Ramesh [Organic Letters, 2013, vol. 15, # 20, p. 5378 - 5381]

40
[ 455-13-0 ]
[ 780-69-8 ]
[ 398-36-7 ]

Yield	Reaction Conditions	Operation in experiment
59%	With copper(l) iodide; cesium fluoride; N,N-dimethyl-2-(diphenylphosphino)aniline In N,N-dimethyl-formamide at 120℃; for 24h; Inert atmosphere;
73 %Spectr.	With copper (II)-fluoride; [PdCl₂(1,3-dimethyl-imidazol-2-ylidene)(AsPh₃)] In N,N-dimethyl-formamide at 110℃; Schlenk technique; Inert atmosphere;

Reference： [1]Gurung, Santosh K.; Thapa, Surendra; Vangala, Adarsh S.; Giri, Ramesh [Organic Letters, 2013, vol. 15, # 20, p. 5378 - 5381]
[2]Delpozo, Juan; Casares, Juan A.; Espinet, Pablo [Chemistry - A European Journal, 2016, vol. 22, # 12, p. 4274 - 4284]

41
[ 455-13-0 ]
[ 780-69-8 ]
[ 581-80-6 ]
[ 398-36-7 ]

Yield	Reaction Conditions	Operation in experiment
	With copper(l) iodide; cesium fluoride In N,N-dimethyl-formamide at 120℃; for 24h; Inert atmosphere;
1: 70 %Spectr. 2: 14 %Spectr.	With copper (II)-fluoride; bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 110℃; Schlenk technique; Inert atmosphere;

42
[ 637-87-6 ]
[ 780-69-8 ]
[ 2051-62-9 ]

Yield	Reaction Conditions	Operation in experiment
96%	With sodium hydroxide In ethanol at 25℃; for 1.5h; Irradiation; Sealed tube; Green chemistry;
96%	With sodium hydroxide In water at 80℃; for 2.5h;	2.8 General Procedure for Hiyama Cross-CouplingReaction General procedure: To a stirring mixture of aryl halide (1 mmol), triethoxyphenylsilane(1.2 mmol) and NaOH (2 mmol) in H2O(4 mL),γ-Fe2O3-Pd-NHC-n-butyl-SO3Na (0.08 or 0.16 mol% based on Pd) was added. The resulting mixture was stirred at 80 °Cfor an appropriate time indicated by TLC monitoring. Aftercooling the reaction to room temperature, the catalyst wasseparated by an external magnet and washed with EtOAc.The product was extracted from the aqueous phase usingEtOAc (3 × 5 mL). After drying the combined organic layersover anhydrous Na2SO4,the solvent was evaporated togive the crude product. Purification of the crude product bycolumn chromatography on silica gel eluted with n-hexane:EtOAc = 30:1 produced the pure products (1-6).
90%	With sodium hydroxide In water at 90℃; for 2h; Green chemistry;

88%	With triethylamine In N,N-dimethyl-formamide at 90℃; for 3h;
48%	With copper(l) iodide; cesium fluoride; N,N-dimethyl-2-(diphenylphosphino)aniline In N,N-dimethyl-formamide at 120℃; for 24h; Inert atmosphere;
48%	With bis-triphenylphosphine-palladium(II) chloride; tetrabutylphosphonium 4-ethoxyvalerate; tetrabutyl ammonium fluoride at 130℃; for 24h; Green chemistry;	General procedure for Hiyama coupling reactions General procedure: In a 4 mL screw-cap vial, 0.5 mmol of the corresponding iodoarene compounds, 1.5 eq of the corresponding silane, 1.5 eq of tetrabutylammonium fluoride (TBAF), 0.01 eq PdCl2(PPh3)2, and 0.8 mL of tetrabutylphosphonium 4-ethoxyvalerate ([TBP][4EtOV]) ionic liquid were mixed and stirred at 130 °C for 24 h. After cooling, the mixture was partitioned between 5 mL of 1 M HCl and 5 mL of pentane. The aqueous phase was extracted subsequently with 3 * 5 mL of pentane. The combined organic phase was washed with brine, dried over MgSO4, and filtered, and the solvent was evaporated under reduced pressure (ca. 1.333 kPa). The residue was purified by chromatography on silica gel (Merck Silicagel 60 (0.063-0.200 mm) for column chromatography (70-230 mesh ASTM)) eluted with n-pentane:EtOAc. The detailed experimental procedure, as well as the characterization of isolated compounds are provided in the Supporting Information.

Reference： [1]Jahanshahi, Roya; Khazaee, Asma; Sobhani, Sara; Sansano, José Miguel [New Journal of Chemistry, 2020, vol. 44, # 27, p. 11513 - 11526]
[2]Chahkamali, Farhad Omarzehi; Sansano, José Miguel; Sobhani, Sara [Catalysis Letters, 2021]
[3]Sobhani, Sara; Hosseini Moghadam, Hadis; Skibsted, Jørgen; Sansano, José Miguel [Green Chemistry, 2020, vol. 22, # 4, p. 1353 - 1365]
[4]Farrokhi, Alireza; Rouzifar, Majid; Sansano, José Miguel; Sobhani, Sara [New Journal of Chemistry, 2021, vol. 45, # 42, p. 19963 - 19976]
[5]Gurung, Santosh K.; Thapa, Surendra; Vangala, Adarsh S.; Giri, Ramesh [Organic Letters, 2013, vol. 15, # 20, p. 5378 - 5381]
[6]Orha, László; Papp, Ábrahám; Tukacs, József M.; Kollár, László; Mika, László T. [Chemical Papers, 2020, vol. 74, # 12, p. 4593 - 4598]

43
[ 153034-86-7 ]
[ 780-69-8 ]
[ 42260-39-9 ]
[ 53344-74-4 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 5378 - 5381

44
[ 780-69-8 ]
[ 32111-21-0 ]
[ 10199-00-5 ]
[ 29460-97-7 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 5378 - 5381

45
[ 570-02-5 ]
[ 780-69-8 ]
[ 64461-92-3 ]

Yield	Reaction Conditions	Operation in experiment
56%	With palladium(II) trifluoroacetate; C30H30N4; silver fluoride; In N,N-dimethyl acetamide; at 100℃; for 2h;	General procedure: To a mixture of aryl(trialkoxy)silane(0.20 mmol), AgF (76.6 mg, 0.60 mmol), Pd(TFA)2 (5.0 mg, 0.015 mmol,7.5 mol %), and ligand 1g (6.7 mg, 0.015 mmol, 7.5 mol %) in DMAc (1.0 mL)was added arylcarboxylic acid (0.40 mmol) at room temperature under an atmosphere of air. After the mixture was stirred at 100?or 110?C for 2-8 h, the mixture was diluted with ethyl acetate and water. The organic layer was washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/EtOAc = 20:1).

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 3184 - 3188

46
[ 780-69-8 ]
[ 5256-79-1 ]

Reference： [1]RSC Advances,2014,vol. 40,p. 41364 - 41370
[2]RSC Advances,2014,vol. 4,p. 41364 - 41370

47
[ 780-69-8 ]
[ 54840-34-5 ]
[ 5707-44-8 ]

Yield	Reaction Conditions	Operation in experiment
88%	With bis(benzonitrile)palladium(II) dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; In tetrahydrofuran; at 50℃; for 3h;	General procedure: A mixture of arylhydrazine (1 mmol), triethoxy(phenyl)silane (1.2 mmol), Pd(PhCN)2Cl2 (5 molpercent) and CSA (camphorsulfonic acid, 1 mmol) was stirred in thesolvent of TBAF (1 M in THF, 1.0 ml) at 50oC for 3 hours under air. After cooling down to room temperature, the insoluble was firstremoved by filtration and then the solvent was removed undera reduced pressure. The cross-coupling products were purified by silica gelchromatography with a mixture of petroleum ether and ethyl acetate. Thecross-coupling products were confirmed by melting point and spectroscopic (1HNMR, 13C NMR and HRMS-EI) analysis, which wereall consistent with the literature results.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 5371 - 5376

48
[ 17672-27-4 ]
[ 780-69-8 ]
[ 2920-38-9 ]

Yield	Reaction Conditions	Operation in experiment
80%	With bis(benzonitrile)palladium(II) dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; In tetrahydrofuran; at 50℃; for 3h;	General procedure: A mixture of arylhydrazine (1 mmol), triethoxy(phenyl)silane (1.2 mmol), Pd(PhCN)2Cl2 (5 mol%) and CSA (camphorsulfonic acid, 1 mmol) was stirred in thesolvent of TBAF (1 M in THF, 1.0 ml) at 50oC for 3 hours under air. After cooling down to room temperature, the insoluble was firstremoved by filtration and then the solvent was removed undera reduced pressure. The cross-coupling products were purified by silica gelchromatography with a mixture of petroleum ether and ethyl acetate. Thecross-coupling products were confirmed by melting point and spectroscopic (1HNMR, 13C NMR and HRMS-EI) analysis, which wereall consistent with the literature results.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 5371 - 5376

49
[ 780-69-8 ]
[ 371-14-2 ]
[ 324-74-3 ]

Yield	Reaction Conditions	Operation in experiment
90%	With bis(benzonitrile)palladium(II) dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; In tetrahydrofuran; at 50℃; for 3h;	General procedure: A mixture of arylhydrazine (1 mmol), triethoxy(phenyl)silane (1.2 mmol), Pd(PhCN)2Cl2 (5 mol%) and CSA (camphorsulfonic acid, 1 mmol) was stirred in thesolvent of TBAF (1 M in THF, 1.0 ml) at 50oC for 3 hours under air. After cooling down to room temperature, the insoluble was firstremoved by filtration and then the solvent was removed undera reduced pressure. The cross-coupling products were purified by silica gelchromatography with a mixture of petroleum ether and ethyl acetate. Thecross-coupling products were confirmed by melting point and spectroscopic (1HNMR, 13C NMR and HRMS-EI) analysis, which wereall consistent with the literature results.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 5371 - 5376

50
[ 780-69-8 ]
[ 1073-69-4 ]
[ 2051-62-9 ]

Yield	Reaction Conditions	Operation in experiment
86%	With bis(benzonitrile)palladium(II) dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride In tetrahydrofuran at 50℃; for 3h;	Typical procedure forthe product General procedure: A mixture of arylhydrazine (1 mmol), triethoxy(phenyl)silane (1.2 mmol), Pd(PhCN)2Cl2 (5 mol%) and CSA (camphorsulfonic acid, 1 mmol) was stirred in thesolvent of TBAF (1 M in THF, 1.0 ml) at 50oC for 3 hours under air. After cooling down to room temperature, the insoluble was firstremoved by filtration and then the solvent was removed undera reduced pressure. The cross-coupling products were purified by silica gelchromatography with a mixture of petroleum ether and ethyl acetate. Thecross-coupling products were confirmed by melting point and spectroscopic (1HNMR, 13C NMR and HRMS-EI) analysis, which wereall consistent with the literature results.

Reference： [1]Zhang, Hui; Wang, Chunjie; Li, Zhiwei; Wang, Ziyun [Tetrahedron Letters, 2015, vol. 56, # 40, p. 5371 - 5376]

51
[ 780-69-8 ]
[ 589-21-9 ]
[ 92-66-0 ]

Yield	Reaction Conditions	Operation in experiment
84%	With bis(benzonitrile)palladium(II) dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride In tetrahydrofuran at 50℃; for 3h;	Typical procedure forthe product General procedure: A mixture of arylhydrazine (1 mmol), triethoxy(phenyl)silane (1.2 mmol), Pd(PhCN)2Cl2 (5 mol%) and CSA (camphorsulfonic acid, 1 mmol) was stirred in thesolvent of TBAF (1 M in THF, 1.0 ml) at 50oC for 3 hours under air. After cooling down to room temperature, the insoluble was firstremoved by filtration and then the solvent was removed undera reduced pressure. The cross-coupling products were purified by silica gelchromatography with a mixture of petroleum ether and ethyl acetate. Thecross-coupling products were confirmed by melting point and spectroscopic (1HNMR, 13C NMR and HRMS-EI) analysis, which wereall consistent with the literature results.

Reference： [1]Zhang, Hui; Wang, Chunjie; Li, Zhiwei; Wang, Ziyun [Tetrahedron Letters, 2015, vol. 56, # 40, p. 5371 - 5376]

52
[ 780-69-8 ]
[ 13116-27-3 ]
[ 1591-31-7 ]

Yield	Reaction Conditions	Operation in experiment
89%	With bis(benzonitrile)palladium(II) dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; In tetrahydrofuran; at 50℃; for 3h;	General procedure: A mixture of arylhydrazine (1 mmol), triethoxy(phenyl)silane (1.2 mmol), Pd(PhCN)2Cl2 (5 mol%) and CSA (camphorsulfonic acid, 1 mmol) was stirred in thesolvent of TBAF (1 M in THF, 1.0 ml) at 50oC for 3 hours under air. After cooling down to room temperature, the insoluble was firstremoved by filtration and then the solvent was removed undera reduced pressure. The cross-coupling products were purified by silica gelchromatography with a mixture of petroleum ether and ethyl acetate. Thecross-coupling products were confirmed by melting point and spectroscopic (1HNMR, 13C NMR and HRMS-EI) analysis, which wereall consistent with the literature results.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 5371 - 5376

53
[ 780-69-8 ]
2-thiophenhydrazine [ No CAS ]
[ 825-55-8 ]

Yield	Reaction Conditions	Operation in experiment
89%	With bis(benzonitrile)palladium(II) dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride In tetrahydrofuran at 50℃; for 3h;	Typical procedure forthe product General procedure: A mixture of arylhydrazine (1 mmol), triethoxy(phenyl)silane (1.2 mmol), Pd(PhCN)2Cl2 (5 mol%) and CSA (camphorsulfonic acid, 1 mmol) was stirred in thesolvent of TBAF (1 M in THF, 1.0 ml) at 50oC for 3 hours under air. After cooling down to room temperature, the insoluble was firstremoved by filtration and then the solvent was removed undera reduced pressure. The cross-coupling products were purified by silica gelchromatography with a mixture of petroleum ether and ethyl acetate. Thecross-coupling products were confirmed by melting point and spectroscopic (1HNMR, 13C NMR and HRMS-EI) analysis, which wereall consistent with the literature results.

Reference： [1]Zhang, Hui; Wang, Chunjie; Li, Zhiwei; Wang, Ziyun [Tetrahedron Letters, 2015, vol. 56, # 40, p. 5371 - 5376]

54
[ 780-69-8 ]
[ 59964-94-2 ]
[ 84-15-1 ]

Yield	Reaction Conditions	Operation in experiment
62%	With bis(benzonitrile)palladium(II) dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride In tetrahydrofuran at 50℃; for 3h;	Typical procedure forthe product General procedure: A mixture of arylhydrazine (1 mmol), triethoxy(phenyl)silane (1.2 mmol), Pd(PhCN)2Cl2 (5 mol%) and CSA (camphorsulfonic acid, 1 mmol) was stirred in thesolvent of TBAF (1 M in THF, 1.0 ml) at 50oC for 3 hours under air. After cooling down to room temperature, the insoluble was firstremoved by filtration and then the solvent was removed undera reduced pressure. The cross-coupling products were purified by silica gelchromatography with a mixture of petroleum ether and ethyl acetate. Thecross-coupling products were confirmed by melting point and spectroscopic (1HNMR, 13C NMR and HRMS-EI) analysis, which wereall consistent with the literature results.

Reference： [1]Zhang, Hui; Wang, Chunjie; Li, Zhiwei; Wang, Ziyun [Tetrahedron Letters, 2015, vol. 56, # 40, p. 5371 - 5376]

55
[ 780-69-8 ]
C₇₂H₆₀O₁₈Si₁₂ [ No CAS ]
[ 5256-79-1 ]
[ 18851-18-8 ]

Reference： [1]Dalton Transactions,2016,vol. 45,p. 1025 - 1039

56
[ 780-69-8 ]
[ 6313-36-6 ]
[ 831-91-4 ]

Yield	Reaction Conditions	Operation in experiment
71%	With copper(II) fluoride dihydrate; palladium diacetate; trifluoroacetic acid In N,N-dimethyl acetamide at 100℃; Schlenk technique; Inert atmosphere;

Reference： [1]Qiao, Zongjun; Jiang, Xuefeng [Organic Letters, 2016, vol. 18, # 7, p. 1550 - 1553]

57
[ 201230-82-2 ]
[ 455-13-0 ]
[ 780-69-8 ]
[ 728-86-9 ]

Yield	Reaction Conditions	Operation in experiment
85%	With dichloro bis(acetonitrile) palladium(II); cesium fluoride In 1-methyl-pyrrolidin-2-one at 80℃; for 6h;	Typical procedure for carbonylative coupling with aryl iodines: General procedure: A mixture of aryl silane (0.5 mmol), aryl iodines (0.5 mmol), PdCl2(MeCN)2 (5 mol%), and CsF (0.5 mmol) was stirred at 80oC for 6 h in NMP (5 mL) under CO (1atm). Afterwards, 2 mL water was added to the reaction solution and then filtered through a filter paper and the solution was extracted by Et2O (2 mL) for three times. The organic phase was combined and evaporated under reduced pressure. The residue was purified on a SiO2 column to afford the desired product (ethyl acetate/hexane).

Reference： [1]Chang, Sheng; Jin, Ying; Zhang, Xiu Rong; Sun, Yong Bing [Tetrahedron Letters, 2016, vol. 57, # 19, p. 2017 - 2020]

58
[ 352-34-1 ]
[ 201230-82-2 ]
[ 780-69-8 ]
[ 345-83-5 ]

Yield	Reaction Conditions	Operation in experiment
93%	With dichloro bis(acetonitrile) palladium(II); cesium fluoride In 1-methyl-pyrrolidin-2-one at 80℃; for 6h;	Typical procedure for carbonylative coupling with aryl iodines: General procedure: A mixture of aryl silane (0.5 mmol), aryl iodines (0.5 mmol), PdCl2(MeCN)2 (5 mol%), and CsF (0.5 mmol) was stirred at 80oC for 6 h in NMP (5 mL) under CO (1atm). Afterwards, 2 mL water was added to the reaction solution and then filtered through a filter paper and the solution was extracted by Et2O (2 mL) for three times. The organic phase was combined and evaporated under reduced pressure. The residue was purified on a SiO2 column to afford the desired product (ethyl acetate/hexane).

Reference： [1]Chang, Sheng; Jin, Ying; Zhang, Xiu Rong; Sun, Yong Bing [Tetrahedron Letters, 2016, vol. 57, # 19, p. 2017 - 2020]

59
[ 201230-82-2 ]
[ 625-99-0 ]
[ 780-69-8 ]
[ 1016-78-0 ]

Yield	Reaction Conditions	Operation in experiment
86%	With dichloro bis(acetonitrile) palladium(II); cesium fluoride; In 1-methyl-pyrrolidin-2-one; at 80℃; under 760.051 Torr; for 6h;	General procedure: A mixture of aryl silane (0.5 mmol), aryl iodines (0.5 mmol), PdCl2(MeCN)2 (5 mol%), and CsF (0.5 mmol) was stirred at 80oC for 6 h in NMP (5 mL) under CO (1atm). Afterwards, 2 mL water was added to the reaction solution and then filtered through a filter paper and the solution was extracted by Et2O (2 mL) for three times. The organic phase was combined and evaporated under reduced pressure. The residue was purified on a SiO2 column to afford the desired product (ethyl acetate/hexane).

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 2017 - 2020

60
[ 615-37-2 ]
[ 201230-82-2 ]
[ 780-69-8 ]
[ 131-58-8 ]

Yield	Reaction Conditions	Operation in experiment
80%	With dichloro bis(acetonitrile) palladium(II); cesium fluoride; In 1-methyl-pyrrolidin-2-one; at 80℃; under 760.051 Torr; for 6h;	General procedure: A mixture of aryl silane (0.5 mmol), aryl iodines (0.5 mmol), PdCl2(MeCN)2 (5 mol%), and CsF (0.5 mmol) was stirred at 80oC for 6 h in NMP (5 mL) under CO (1atm). Afterwards, 2 mL water was added to the reaction solution and then filtered through a filter paper and the solution was extracted by Et2O (2 mL) for three times. The organic phase was combined and evaporated under reduced pressure. The residue was purified on a SiO2 column to afford the desired product (ethyl acetate/hexane).

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 2017 - 2020

61
[ 201230-82-2 ]
[ 615-41-8 ]
[ 780-69-8 ]
[ 5162-03-8 ]

Yield	Reaction Conditions	Operation in experiment
83%	With dichloro bis(acetonitrile) palladium(II); cesium fluoride; In 1-methyl-pyrrolidin-2-one; at 80℃; under 760.051 Torr; for 6h;	General procedure: A mixture of aryl silane (0.5 mmol), aryl iodines (0.5 mmol), PdCl2(MeCN)2 (5 mol%), and CsF (0.5 mmol) was stirred at 80oC for 6 h in NMP (5 mL) under CO (1atm). Afterwards, 2 mL water was added to the reaction solution and then filtered through a filter paper and the solution was extracted by Et2O (2 mL) for three times. The organic phase was combined and evaporated under reduced pressure. The residue was purified on a SiO2 column to afford the desired product (ethyl acetate/hexane).

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 2017 - 2020

62
[ 201230-82-2 ]
[ 827-15-6 ]
[ 780-69-8 ]
[ 1536-23-8 ]

Yield	Reaction Conditions	Operation in experiment
75%	With dichloro bis(acetonitrile) palladium(II); cesium fluoride; In 1-methyl-pyrrolidin-2-one; at 80℃; under 760.051 Torr; for 6h;	General procedure: A mixture of aryl silane (0.5 mmol), aryl iodines (0.5 mmol), PdCl2(MeCN)2 (5 mol%), and CsF (0.5 mmol) was stirred at 80oC for 6 h in NMP (5 mL) under CO (1atm). Afterwards, 2 mL water was added to the reaction solution and then filtered through a filter paper and the solution was extracted by Et2O (2 mL) for three times. The organic phase was combined and evaporated under reduced pressure. The residue was purified on a SiO2 column to afford the desired product (ethyl acetate/hexane).

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 2017 - 2020

63
[ 5029-67-4 ]
[ 201230-82-2 ]
[ 780-69-8 ]
[ 91-02-1 ]

Yield	Reaction Conditions	Operation in experiment
72%	With dichloro bis(acetonitrile) palladium(II); cesium fluoride In 1-methyl-pyrrolidin-2-one at 80℃; for 6h;	Typical procedure for carbonylative coupling with aryl iodines: General procedure: A mixture of aryl silane (0.5 mmol), aryl iodines (0.5 mmol), PdCl2(MeCN)2 (5 mol%), and CsF (0.5 mmol) was stirred at 80oC for 6 h in NMP (5 mL) under CO (1atm). Afterwards, 2 mL water was added to the reaction solution and then filtered through a filter paper and the solution was extracted by Et2O (2 mL) for three times. The organic phase was combined and evaporated under reduced pressure. The residue was purified on a SiO2 column to afford the desired product (ethyl acetate/hexane).

Reference： [1]Chang, Sheng; Jin, Ying; Zhang, Xiu Rong; Sun, Yong Bing [Tetrahedron Letters, 2016, vol. 57, # 19, p. 2017 - 2020]

64
[ 201230-82-2 ]
[ 402-43-7 ]
[ 780-69-8 ]
[ 728-86-9 ]

Yield	Reaction Conditions	Operation in experiment
84%	With dichloro bis(acetonitrile) palladium(II); cesium fluoride In 1-methyl-pyrrolidin-2-one at 100℃; for 6h;	Typical procedure for carbonylative coupling with aryl bromides: General procedure: A mixture of aryl silane (0.5 mmol), aryl bromides (0.5 mmol), PdCl2(MeCN)2 (5 mol%), and CsF (0.5 mmol) was stirred at 100oC for 6 h in NMP under CO (1atm) (5 mL). Afterwards, 2 mL water was added to the reaction solution and then filtered through a filter paper and the solution was extracted by Et2O (2 mL) for three times. The organic phase was combined and evaporated under reduced pressure. The residue was purified on a SiO2 column to afford the desired product(ethyl acetate/hexane).

Reference： [1]Chang, Sheng; Jin, Ying; Zhang, Xiu Rong; Sun, Yong Bing [Tetrahedron Letters, 2016, vol. 57, # 19, p. 2017 - 2020]

65
[ 201230-82-2 ]
[ 780-69-8 ]
[ 460-00-4 ]
[ 345-83-5 ]

Yield	Reaction Conditions	Operation in experiment
88%	With dichloro bis(acetonitrile) palladium(II); cesium fluoride In 1-methyl-pyrrolidin-2-one at 100℃; for 6h;	Typical procedure for carbonylative coupling with aryl bromides: General procedure: A mixture of aryl silane (0.5 mmol), aryl bromides (0.5 mmol), PdCl2(MeCN)2 (5 mol%), and CsF (0.5 mmol) was stirred at 100oC for 6 h in NMP under CO (1atm) (5 mL). Afterwards, 2 mL water was added to the reaction solution and then filtered through a filter paper and the solution was extracted by Et2O (2 mL) for three times. The organic phase was combined and evaporated under reduced pressure. The residue was purified on a SiO2 column to afford the desired product(ethyl acetate/hexane).

Reference： [1]Chang, Sheng; Jin, Ying; Zhang, Xiu Rong; Sun, Yong Bing [Tetrahedron Letters, 2016, vol. 57, # 19, p. 2017 - 2020]

66
[ 201230-82-2 ]
[ 623-00-7 ]
[ 780-69-8 ]
[ 1503-49-7 ]

Yield	Reaction Conditions	Operation in experiment
90%	With dichloro bis(acetonitrile) palladium(II); cesium fluoride In 1-methyl-pyrrolidin-2-one at 100℃; for 6h;	Typical procedure for carbonylative coupling with aryl bromides: General procedure: A mixture of aryl silane (0.5 mmol), aryl bromides (0.5 mmol), PdCl2(MeCN)2 (5 mol%), and CsF (0.5 mmol) was stirred at 100oC for 6 h in NMP under CO (1atm) (5 mL). Afterwards, 2 mL water was added to the reaction solution and then filtered through a filter paper and the solution was extracted by Et2O (2 mL) for three times. The organic phase was combined and evaporated under reduced pressure. The residue was purified on a SiO2 column to afford the desired product(ethyl acetate/hexane).

Reference： [1]Chang, Sheng; Jin, Ying; Zhang, Xiu Rong; Sun, Yong Bing [Tetrahedron Letters, 2016, vol. 57, # 19, p. 2017 - 2020]

67
[ 108-37-2 ]
[ 201230-82-2 ]
[ 780-69-8 ]
[ 1016-78-0 ]

Yield	Reaction Conditions	Operation in experiment
80%	With dichloro bis(acetonitrile) palladium(II); cesium fluoride; In 1-methyl-pyrrolidin-2-one; at 100℃; under 760.051 Torr; for 6h;	General procedure: A mixture of aryl silane (0.5 mmol), aryl bromides (0.5 mmol), PdCl2(MeCN)2 (5 mol%), and CsF (0.5 mmol) was stirred at 100oC for 6 h in NMP under CO (1atm) (5 mL). Afterwards, 2 mL water was added to the reaction solution and then filtered through a filter paper and the solution was extracted by Et2O (2 mL) for three times. The organic phase was combined and evaporated under reduced pressure. The residue was purified on a SiO2 column to afford the desired product(ethyl acetate/hexane).

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 2017 - 2020

68
[ 694-80-4 ]
[ 201230-82-2 ]
[ 780-69-8 ]
[ 5162-03-8 ]

Yield	Reaction Conditions	Operation in experiment
78%	With dichloro bis(acetonitrile) palladium(II); cesium fluoride; In 1-methyl-pyrrolidin-2-one; at 100℃; under 760.051 Torr; for 6h;	General procedure: A mixture of aryl silane (0.5 mmol), aryl bromides (0.5 mmol), PdCl2(MeCN)2 (5 mol%), and CsF (0.5 mmol) was stirred at 100oC for 6 h in NMP under CO (1atm) (5 mL). Afterwards, 2 mL water was added to the reaction solution and then filtered through a filter paper and the solution was extracted by Et2O (2 mL) for three times. The organic phase was combined and evaporated under reduced pressure. The residue was purified on a SiO2 column to afford the desired product(ethyl acetate/hexane).

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 2017 - 2020

69
[ 201230-82-2 ]
[ 95-46-5 ]
[ 780-69-8 ]
[ 131-58-8 ]

Yield	Reaction Conditions	Operation in experiment
85%	With dichloro bis(acetonitrile) palladium(II); cesium fluoride In 1-methyl-pyrrolidin-2-one at 100℃; for 6h;	Typical procedure for carbonylative coupling with aryl bromides: General procedure: A mixture of aryl silane (0.5 mmol), aryl bromides (0.5 mmol), PdCl2(MeCN)2 (5 mol%), and CsF (0.5 mmol) was stirred at 100oC for 6 h in NMP under CO (1atm) (5 mL). Afterwards, 2 mL water was added to the reaction solution and then filtered through a filter paper and the solution was extracted by Et2O (2 mL) for three times. The organic phase was combined and evaporated under reduced pressure. The residue was purified on a SiO2 column to afford the desired product(ethyl acetate/hexane).

Reference： [1]Chang, Sheng; Jin, Ying; Zhang, Xiu Rong; Sun, Yong Bing [Tetrahedron Letters, 2016, vol. 57, # 19, p. 2017 - 2020]

70
[ 5153-40-2 ]
[ 201230-82-2 ]
[ 780-69-8 ]
[ 20386-33-8 ]

Yield	Reaction Conditions	Operation in experiment
76%	With dichloro bis(acetonitrile) palladium(II); cesium fluoride; In 1-methyl-pyrrolidin-2-one; at 100℃; under 760.051 Torr; for 6h;	General procedure: A mixture of aryl silane (0.5 mmol), aryl bromides (0.5 mmol), PdCl2(MeCN)2 (5 mol%), and CsF (0.5 mmol) was stirred at 100oC for 6 h in NMP under CO (1atm) (5 mL). Afterwards, 2 mL water was added to the reaction solution and then filtered through a filter paper and the solution was extracted by Et2O (2 mL) for three times. The organic phase was combined and evaporated under reduced pressure. The residue was purified on a SiO2 column to afford the desired product(ethyl acetate/hexane).

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 2017 - 2020

71
[ 344-04-7 ]
[ 201230-82-2 ]
[ 780-69-8 ]
[ 1536-23-8 ]

Yield	Reaction Conditions	Operation in experiment
79%	With dichloro bis(acetonitrile) palladium(II); cesium fluoride In 1-methyl-pyrrolidin-2-one at 100℃; for 6h;	Typical procedure for carbonylative coupling with aryl bromides: General procedure: A mixture of aryl silane (0.5 mmol), aryl bromides (0.5 mmol), PdCl2(MeCN)2 (5 mol%), and CsF (0.5 mmol) was stirred at 100oC for 6 h in NMP under CO (1atm) (5 mL). Afterwards, 2 mL water was added to the reaction solution and then filtered through a filter paper and the solution was extracted by Et2O (2 mL) for three times. The organic phase was combined and evaporated under reduced pressure. The residue was purified on a SiO2 column to afford the desired product(ethyl acetate/hexane).

Reference： [1]Chang, Sheng; Jin, Ying; Zhang, Xiu Rong; Sun, Yong Bing [Tetrahedron Letters, 2016, vol. 57, # 19, p. 2017 - 2020]

72
[ 125533-82-6 ]
[ 201230-82-2 ]
[ 780-69-8 ]
[ 174150-58-4 ]

Yield	Reaction Conditions	Operation in experiment
68%	With dichloro bis(acetonitrile) palladium(II); cesium fluoride; In 1-methyl-pyrrolidin-2-one; at 100℃; under 760.051 Torr; for 6h;	General procedure: A mixture of aryl silane (0.5 mmol), aryl bromides (0.5 mmol), PdCl2(MeCN)2 (5 mol%), and CsF (0.5 mmol) was stirred at 100oC for 6 h in NMP under CO (1atm) (5 mL). Afterwards, 2 mL water was added to the reaction solution and then filtered through a filter paper and the solution was extracted by Et2O (2 mL) for three times. The organic phase was combined and evaporated under reduced pressure. The residue was purified on a SiO2 column to afford the desired product(ethyl acetate/hexane).

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 2017 - 2020

73
[ 29835-27-6 ]
[ 780-69-8 ]
[ 14635-91-7 ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 5244 - 5249
[2]Tetrahedron Letters,2016,vol. 57,p. 4581 - 4584

74
[ 32340-38-8 ]
[ 780-69-8 ]
[ 15784-39-1 ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 5244 - 5249

75
[ 1357155-90-8 ]
[ 780-69-8 ]
[ 42497-80-3 ]

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 4581 - 4584
[2]Journal of Organic Chemistry,2016,vol. 81,p. 5244 - 5249

76
[ 780-69-8 ]
[ 59608-01-4 ]
[ 13238-38-5 ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 5244 - 5249

77
[ 780-69-8 ]
[ 868-85-9 ]
[ 2240-41-7 ]

Reference： [1]Chemical Communications,2017,vol. 53,p. 956 - 958

78
[ 585-79-5 ]
[ 780-69-8 ]
[ 2113-58-8 ]

Reference： [1]Catalysis Communications,2018,vol. 103,p. 92 - 95

79
[ 780-69-8 ]
[ 830-09-1 ]
[ 4333-75-9 ]

Yield	Reaction Conditions	Operation in experiment
58%	With copper (II)-fluoride; palladium diacetate; cesium fluoride; p-benzoquinone; 4,4'-di-tert-butyl-2,2'-bipyridine In dimethyl sulfoxide at 150℃; for 5h; Molecular sieve; Inert atmosphere;	58 Example 56-60 In the 5mL reactor, replace it with argon three times, then add 1mm magnets,P-methoxycinnamic acid (0.4 mmol), catalyst Pd(OAc) 2 (0.04 mmol),CuF2 oxidant (0.6 mmol), ligand L7 (0.06 mmol),1 equivalent of cesium fluoride (0.4 mmol), 1 equivalent of p-benzoquinone (BQ, 0.4 mmol),75 mg molecular sieve (water removal), the reactor was evacuated and replaced with argon three times.Then, phenyltriethoxysilane (0.8 mmol) and DMSO (2 ml) were mixed and added to the reactor, and then an argon balloon was inserted, and then the reactor was placed in an oil bath previously heated to 150 ° C. The reaction is carried out at different temperatures for different times. After the reaction is over,The reaction solution was filtered through celite, and the filtrate was thThe aqueous phase is back extracted twice with ethyl acetate or dichloromethane, then the organic phases are combined.It was dried over anhydrous magnesium sulfate. The dried organic phase was spun on a vacuum rotary evaporator.The objective product was isolated by chromatography on a thin layer of silica gel, and yield was calculated.

Reference： [1]Current Patent Assignee: ZHENGZHOU DERUI PHARMACEUTICAL TECH - CN108586211, 2018, A Location in patent: Paragraph 0043; 0048; 0056; 0068; 0071; 0079; 0094; 0095

80
[ 1506-76-9 ]
[ 780-69-8 ]
[ 71-91-0 ]
[ 33513-42-7 ]
C₁₂₀H₇₈O₂₄Si₆^(6-)*4C₈H₂₀N⁽¹⁺⁾*2Br^(1-)*70H₂O*4Cs⁽¹⁺⁾ [ No CAS ]

Reference： [1]Chemical Communications,2018,vol. 54,p. 11877 - 11880

81
[ 392-56-3 ]
[ 780-69-8 ]
[ 784-14-5 ]

Yield	Reaction Conditions	Operation in experiment
38%	With [Ni₂(1,3-diisopropyl-imidazolin-2-ylidene)₄(μ-1,5-cyclooctadiene)] In toluene at 110℃; for 48h; Inert atmosphere;

Reference： [1]Kuntze-Fechner, Maximilian W.; Kerpen, Christoph; Schmidt, David; Häring, Mathias; Radius, Udo [European Journal of Inorganic Chemistry, 2019, vol. 2019, # 13, p. 1767 - 1775]

82
[ 101-55-3 ]
[ 780-69-8 ]
[ 3933-94-6 ]

Reference： [1]Israel Journal of Chemistry,2019

83
[ 780-69-8 ]
[ 103962-05-6 ]
[ 71274-84-5 ]

Yield	Reaction Conditions	Operation in experiment
61%	With bis-triphenylphosphine-palladium(II) chloride; tetrabutylphosphonium 4-ethoxyvalerate; tetrabutyl ammonium fluoride; at 130℃; for 24h;Green chemistry;	General procedure: In a 4 mL screw-cap vial, 0.5 mmol of the corresponding iodoarene compounds, 1.5 eq of the corresponding silane, 1.5 eq of tetrabutylammonium fluoride (TBAF), 0.01 eq PdCl2(PPh3)2, and 0.8 mL of tetrabutylphosphonium 4-ethoxyvalerate ([TBP][4EtOV]) ionic liquid were mixed and stirred at 130 C for 24 h. After cooling, the mixture was partitioned between 5 mL of 1 M HCl and 5 mL of pentane. The aqueous phase was extracted subsequently with 3 * 5 mL of pentane. The combined organic phase was washed with brine, dried over MgSO4, and filtered, and the solvent was evaporated under reduced pressure (ca. 1.333 kPa). The residue was purified by chromatography on silica gel (Merck Silicagel 60 (0.063-0.200 mm) for column chromatography (70-230 mesh ASTM)) eluted with n-pentane:EtOAc. The detailed experimental procedure, as well as the characterization of isolated compounds are provided in the Supporting Information.

Reference： [1]Chemical Papers,2020,vol. 74,p. 4593 - 4598

84
[ 352-34-1 ]
[ 780-69-8 ]
[ 324-74-3 ]

Yield	Reaction Conditions	Operation in experiment
68%	With bis-triphenylphosphine-palladium(II) chloride; tetrabutylphosphonium 4-ethoxyvalerate; tetrabutyl ammonium fluoride; at 130℃; for 24h;Green chemistry;	General procedure: In a 4 mL screw-cap vial, 0.5 mmol of the corresponding iodoarene compounds, 1.5 eq of the corresponding silane, 1.5 eq of tetrabutylammonium fluoride (TBAF), 0.01 eq PdCl2(PPh3)2, and 0.8 mL of tetrabutylphosphonium 4-ethoxyvalerate ([TBP][4EtOV]) ionic liquid were mixed and stirred at 130 C for 24 h. After cooling, the mixture was partitioned between 5 mL of 1 M HCl and 5 mL of pentane. The aqueous phase was extracted subsequently with 3 * 5 mL of pentane. The combined organic phase was washed with brine, dried over MgSO4, and filtered, and the solvent was evaporated under reduced pressure (ca. 1.333 kPa). The residue was purified by chromatography on silica gel (Merck Silicagel 60 (0.063-0.200 mm) for column chromatography (70-230 mesh ASTM)) eluted with n-pentane:EtOAc. The detailed experimental procedure, as well as the characterization of isolated compounds are provided in the Supporting Information.

Reference： [1]Chemical Papers,2020,vol. 74,p. 4593 - 4598

85
[ 780-69-8 ]
[ 104830-06-0 ]
[ 87109-10-2 ]

Yield	Reaction Conditions	Operation in experiment
55%	With bis-triphenylphosphine-palladium(II) chloride; tetrabutylphosphonium 4-ethoxyvalerate; tetrabutyl ammonium fluoride at 130℃; for 24h; Green chemistry;	General procedure for Hiyama coupling reactions General procedure: In a 4 mL screw-cap vial, 0.5 mmol of the corresponding iodoarene compounds, 1.5 eq of the corresponding silane, 1.5 eq of tetrabutylammonium fluoride (TBAF), 0.01 eq PdCl2(PPh3)2, and 0.8 mL of tetrabutylphosphonium 4-ethoxyvalerate ([TBP][4EtOV]) ionic liquid were mixed and stirred at 130 °C for 24 h. After cooling, the mixture was partitioned between 5 mL of 1 M HCl and 5 mL of pentane. The aqueous phase was extracted subsequently with 3 * 5 mL of pentane. The combined organic phase was washed with brine, dried over MgSO4, and filtered, and the solvent was evaporated under reduced pressure (ca. 1.333 kPa). The residue was purified by chromatography on silica gel (Merck Silicagel 60 (0.063-0.200 mm) for column chromatography (70-230 mesh ASTM)) eluted with n-pentane:EtOAc. The detailed experimental procedure, as well as the characterization of isolated compounds are provided in the Supporting Information.

Reference： [1]Orha, László; Papp, Ábrahám; Tukacs, József M.; Kollár, László; Mika, László T. [Chemical Papers, 2020, vol. 74, # 12, p. 4593 - 4598]

86
1-(3,4-difluorobenzoyl)piperidine-2,6-dione [ No CAS ]
[ 780-69-8 ]
[ 85118-07-6 ]

Yield	Reaction Conditions	Operation in experiment
82%	With lithium acetate; palladium diacetate; triethylamine tris(hydrogen fluoride); tricyclohexylphosphine In 1,4-dioxane; water at 90℃; for 6h;

Reference： [1]Idris, Muhammad Aliyu; Lee, Sunwoo [Organic Letters, 2020, vol. 22, # 23, p. 9190 - 9195]

87
[ 591-50-4 ]
[ 780-69-8 ]
[ 127-63-9 ]

Yield	Reaction Conditions	Operation in experiment
82%	With tetrakis(acetonitrile)copper(I)tetrafluoroborate; 1,4-diazabicyclo[2.2.2]octane-triethylenediamine-bis(sulfur dioxide); tetrabutyl ammonium fluoride; N,N`-dimethylethylenediamine In acetonitrile at 120℃; for 24h; Glovebox; Inert atmosphere;

Reference： [1]Adenot, Aurélien; Anthore-Dalion, Lucile; Nicolas, Emmanuel; Berthet, Jean-Claude; Thuéry, Pierre; Cantat, Thibault [Chemistry - A European Journal, 2021, vol. 27, # 72, p. 18047 - 18053]

88
[ 780-69-8 ]
[ 15164-44-0 ]
[ 66-39-7 ]

Reference： [1]Chemistry - A European Journal,2021,vol. 27,p. 18047 - 18053

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Precautionary Statements-General
Code	Phrase
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Prevention
Code	Phrase
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P222	Do not allow contact with air.
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Code	Phrase
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P321
P322
P330	Rinse mouth.
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P378
P380	Evacuate area.
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P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
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P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
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P337 + P313	IF eye irritation persists: Get medical advice/attention.
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Disposal
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
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H231	May react explosively even in the absence of air at elevated pressure and/or temperature
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H242	Heating may cause a fire
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H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
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H315	Causes skin irritation
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H317	May cause an allergic skin reaction
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H319	Causes serious eye irritation
H320	Causes eye irritation
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H332	Harmful if inhaled
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H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
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H336	May cause drowsiness or dizziness
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H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 780-69-8 ] {[proInfo.proName]}

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[ 780-69-8 ] Synthesis Path-Upstream 1~2

[ 780-69-8 ] Synthesis Path-Downstream 1~88

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Organosilicon

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[ 780-69-8 ]