250220-36-1|(3-Phenyl-1H-inden-1-ylidene)bis(tricyclohexylphosphine)ruthenium(II)dichloride| Ambeed

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Quality Control of [ 250220-36-1 ] Purity: 97% SDS Specification

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Product Details of [ 250220-36-1 ]

CAS No. :	250220-36-1
Formula :	C₅₁H₇₆Cl₂P₂Ru
M.W :	923.07
SMILES Code :	[Ru+2]=C1C=C(C2=CC=CC=C2)C3=C1C=CC=C3.P(C4CCCCC4)(C5CCCCC5)C6CCCCC6.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9.[Cl-].[Cl-]
MDL No. :	MFCD07369034
InChI Key :	UZAFZWUWHHFWOK-UHFFFAOYSA-L
Pubchem ID :	11029366

Safety of [ 250220-36-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313

Application In Synthesis of [ 250220-36-1 ]

* 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.

Downstream synthetic route of [ 250220-36-1 ]

[ 250220-36-1 ] Synthesis Path-Downstream 1~35

1
[ 250220-36-1 ]
[ 66021-95-2 ]
RuCl₂(P(C₆H₁₁)3)(C₆H₅C₉H₅CHCC₆H₄OCH(CH₃)2) [ No CAS ]

References: [1]Organometallics,2005,vol. 24,p. 4065 - 4071.

2
[ 250220-36-1 ]
[ 260054-47-5 ]
[1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro-(3-phenyl-1H-inden-1-ylidene)(tricyclohexylphosphine)ruthenium(II) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In toluene; at 70℃; for 15h;Schlenk technique; Inert atmosphere;	Absolute toluene (50 mL),complex 8 (4.40 g, 4.75 mmol), and 1,3-bis(2,4,6-trimethylphenyl)-2-trichloromethylimidazolidine (9) 2.41 g (5.70 mmol) were placed into a Schlenk flask(100 mL). The mixture was heated under argon at 70 C for 15 h, then was cooled tor.t and styrene 4a, 4e, 5e or 7 (7.14 mmol) was added in an argon stream. Themixture was heated at reflux under an inert atmosphere for 6 h. Toluene wasevaporated under reduced pressure and the residue was suspended in hexane (30mL). The obtained mixture was kept at -20 C for 10 h. The precipitate was filteredoff and washed with hexane (3 × 12 mL) and then with methanol (2 × 12 mL) to giveafter drying under vacuum a light green powder of pure catalyst (11), which arestable at rt in air at least for 4 years (see the Discussion). System for TLC is hexane :EtOAc, 4:1. Rf 0.3-0.4 (Sorbfil TLC plates were used). The spectroscopic data andphysical properties of complexes 11a,b correspond to the published earlier [8].

References: [1]European Journal of Inorganic Chemistry,2008,p. 432 - 440.
[2]Organometallics,2020,vol. 39,p. 4599 - 4607.
[3]Beilstein Journal of Organic Chemistry,2019,vol. 15,p. 769 - 779.

3
[ 110-86-1 ]
[ 250220-36-1 ]
Cl₂Ru(PCy₃)(pyridine)2(3-phenylindenylidene) [ No CAS ]

References: [1]Journal of Organometallic Chemistry,2006,vol. 691,p. 5444 - 5447.

4
[ 250220-36-1 ]
[ 258278-28-3 ]
RuCl₂(C₉H₅Ph)(tricyclohexylphosphine)(1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene) [ No CAS ]

References: [1]Organometallics,2009,vol. 28,p. 2848 - 2854.

5
[ 250220-36-1 ]
[ 1191099-53-2 ]
RuCl₂(=CH(o-OCH(Me)CO-N-pyrrolidine)Ph)(PCy₃) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	In toluene; at 100℃; for 16h;	A solution of 20.00 g (21.70 mmol) of <strong>[250220-36-1][RuCl2(PCy3)2(3-phenyl-indenylidene)]</strong> (commercially available from Umicore AG, D-63457 Hanau- Wolfgang) and 5.32 g (21.70 mmol) of 1- Pyrrolidin-l-yl-2-(2-vinylphenoxy)-propan-l-one in 200 ml of toluene was stirred for 16 h at 1000C. The dark green solution was concentrated to a total volume of 100 ml, 200 ml of pentane were added and the formed dark green suspension was stirred for 30 min in an ice-bath. After filtration, the residual curde product K was washed with 110 ml of pentane / toluene 11 :1 and successively with 100 ml of pentane and dried under vacuum at room temperature to yield 8.93 g (60%) of the title compound as a green powder. MS: 683.2 (M t++). 3 'IP-NMR (CDCl3): δ 56.6 ppm.

References: [1]Patent: WO2009/124853,2009,A1 .Location in patent: Page/Page column 49.

6
[ 250220-36-1 ]
[ 3246-73-9 ]
C₄₇H₅₅ClNOPRu [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With silver carbonate; In tetrahydrofuran; for 72h;Inert atmosphere;	The stoichiometric amounts of indenylidene first-generation catalyst (7), the corresponding Schiff base ligand, and silver(I) carbonate were added to a Schlenk flask (50-250 ml). The flask was evacuated and backfilled with argon. Dry THF (20 ml) was then transferred to the Schlenk flask (still under argon) and stirred for a period of 6-72 h. The reaction mixture was cooled at 0 C. whereas the white precipitate of PCy3AgCl (by-product) was removed by filtration. The filtrate was collected in a Schlenk flask (250 ml), and the solvent was removed by evaporation under reduced pressure.EXAMPLE 1Complex 8 (Table 1; entry 22): Indenylidene first-generation catalyst (7) (500 mg, 0.54 mmol), 2-[(2-methylphenylimino)methyl]phenol (pKa: 8.93+/-0.35) (113 mg, 0.54 mmol), silver(I) carbonate (74.48 g, 0.27 mmol), and THF (10 ml) were reacted as described above for 72 h. The reaction mixture was investigated on 1H and 31P NMR, which revealed quantitative transformation to complex 8, namely 98%, of title complex.1H NMR (in dichloromethane-d2, 295 K)(δ [ppm], multiplicity, intensity, J [Hz], assignment):8.38 (d, [1H], J=7.4 Hz, H-22); 7.84 (d, [1H], J=7.0 Hz, H-7); 7.71 (d, [2H], J=7.4 Hz, H-25); 7.51 (t, [1H], J=7.1 Hz, H-27), 7.40 (d, [1H], J=7.5 Hz, H-19); 7.36 (dd, [2H], H-26); 7.30 (dd, [1H], H-12); 7.26-7.21 (unresolved multiplets, [5H]: H-4, H-21, H-9, H-10, H-11);7.20 (d, [1H], J=8.8 Hz, H-5); 7.04 (d, [1H], J=8.8 Hz, H-2); 6.88 (s, [1H], H-16); 6.81 (dd, [1H], J=5.5 Hz, H-20); 6.50 (t, [1H], J=7.5 Hz, H-3); 2.52 (q, [3H], J=11.4 Hz, PCy3); 2.42 (s, 3H, H-14); 1.95-1.54 (m, [20H], CH2 of PCy3); 1.30-1.23 (m, [20H], CH2 of PCy3).13C NMR: 292.8 (b.s, C-15); 170.5 (s, C-1); 165.3 (s, C-7); 154.3 (s, C-8); 140.9 (s, C-18); 139.6 (s, C-17); 136.6 (d, C-16); 136.0 (s, C-2); 133.5 (s, C-4); 131.8 (s, C-23); 131.2 (s, C-13); 130.4 (s, C-13); 129.4 (s, C-12); 129.1 (s, C-19); 129.0 (s, C-26); 128.9 (C-9-11); 128.9 (s, C-21); 128.2 (s, C-22); 128.0 (s, C-27); 127.4 (s, C-24); 126.3 (s, C-25); 125.5 (C-9-11); 124.7 (s, C-20); 122.4 (s, C-5); 117.5 (s, C-6); 117.3 (C-9-11); 114.4 (s, C-3); 33.1 (s, C-14); cyclohexyl resonances: 33.1 (d, J=19.7 Hz); 29.8 (s); 29.3 (s); 27.8 (dd, J1=30 Hz, J1=10 Hz); 26.6 (dd, J1=82 Hz, J1=11 Hz); 26.5 (s).31P NMR: 37.24 ppm (broad singlet)
	With silver carbonate; In tetrahydrofuran; for 72h;Inert atmosphere;	The stoichiometric amounts of indenylidene first-generation catalyst (7), the corresponding Schiff base ligand, and silver(I) carbonate were added to a Schlenk flask (50-250 ml). The flask was evacuated and backfilled with argon. Dry THF (20 ml) was then transferred to the Schlenk flask (still under argon) and stirred for a period of 6-72 h. The reaction mixture was cooled at 0C whereas the white precipitate of PCy3AgCl (by-product) was removed by filtration. The filtrate was collected in a Schlenk flask (250 ml), and the solvent was removed by evaporation under reduced pressure.Example 1 Complex 8 (Table 1; entry 22): Indenylidene first-generation catalyst (7) (500 mg, 0.54 mmol), 2-[(2-methylphenylimino)methyl]phenol (pKa: 8.93 +/- 0.35) (113 mg, 0.54 mmol), silver(I) carbonate (74.48 g, 0.27 mmol), and THF (10 ml) were reacted as described above for 72 h. The reaction mixture was investigated on 1H and 31P NMR, which revealed quantitative transformation to complex 8, namely 98%, of title complex. 1H NMR (in dichloromethane-d2, 295 K) (δ [ppm], multiplicity, intensity, J [Hz], assignment): 8. 38 (d, [1 H], J = 7.4 Hz, H-22); 7.84 (d, [1H], J = 7.0 Hz, H-7); 7.71 (d, [2H], J = 7.4 Hz, H-25); 7.51 (t, [1H], J = 7.1 Hz, H-27), 7.40 (d, [1H], J = 7.5 Hz,H-19); 7.36 (dd, [2H], H-26); 7.30 (dd, [1 H], H-12); 7.26 - 7.21 (unresolved multiplets, [5H]: H-4, H-21, H-9, H-10, H-11); 7.20 (d, [1H], J = 8.8 Hz, H-5); 7.04 (d, [1H], J = 8.8 Hz, H-2); 6.88 (s, [1 H], H-16); 6.81 (dd, [1 H], J = 5.5 Hz, H-20); 6.50 (t, [1 H], J = 7.5 Hz, H-3); 2.52 (q, [3H], J = 11.4 Hz, PCy3); 2.42 (s, 3H, H-14); 1.95-1.54 (m, [20H], CH2 of PCy3); 1.30-1.23 (m, [20H], CH2 of PCy3). 13C NMR: 292.8 (b.s, C-15); 170.5 (s, C-1); 165.3 (s, C-7); 154.3(s, C-8); 140.9 (s, C-18); 139.6 (s, C-17); 136.6 (d, C-16); 136.0 (s, C-2); 133.5 (s, C-4); 131.8 (s, C-23); 131.2 (s, C-13); 130.4 (s, C-13); 129.4 (s, C-12); 129.1 (s, C-19); 129.0 (s, C-26); 128.9 (C-9-11); 128.9 (s, C-21); 128.2 (s, C-22); 128.0 (s, C-27); 127.4 (s, C-24); 126.3 (s, C-25); 125.5 (C-9-11); 124.7 (s, C-20); 122.4 (s, C-5); 117.5 (s, C-6); 117.3 (C-9-11); 114.4 (s, C-3); 33.1 (s, C-14); cyclohexyl resonances: 33.1 (d, J = 19.7 Hz); 29.8 (s); 29.3 (s) ; 27.8 (dd, J1 = 30 Hz, J1 = 10 Hz); 26.6 (dd, J1 = 82 Hz, J1 = 11 Hz); 26.5 (s). 31P NMR: 37.24 ppm (broad singlet)
	With silver carbonate; In tetrahydrofuran; for 72h;Inert atmosphere;	Indenylidene first-generation catalyst (7) (500 mg, 0.54 mmol), 2-[(2-methylphenylimino)methyl]phenol (pKa: 8.93 +/- 0.35) (113 mg, 0.54 mmol), silver(I) carbonate (74.48 g, 0.27 mmol), and THF (10 ml) were reacted as described above for 72 h. The reaction mixture was investigated on 1H and 31P NMR, which revealed quantitative transformation to complex 8, namely 98%, of title complex. 1H NMR (in dichloromethane-d2, 295 K) (δ [ppm], multiplicity, intensity, J [Hz], assignment): 8. 38 (d, [1 H], J = 7.4 Hz, H-22); 7.84 (d, [1 H], J = 7.0 Hz, H-7); 7.71 (d, [2H], J = 7.4 Hz, H-25); 7.51 (t, [1 H], J = 7.1 Hz, H-27), 7.40 (d, [1 H], J = 7.5 Hz,H-19); 7.36 (dd, [2H], H-26); 7.30 (dd, [1 H], H-12); 7.26 - 7.21 (unresolved multiplets, [5H]: H-4, H-21, H-9, H-10, H-11); 7.20 (d, [1H], J = 8.8 Hz, H-5); 7.04 (d, [1 H], J = 8.8 Hz, H-2); 6.88 (s, [1 H], H-16); 6.81 (dd, [1 H], J = 5.5 Hz, H-20); 6.50 (t, [1 H], J = 7.5 Hz, H-3); 2.52 (q, [3H], J = 11.4 Hz, PCy3); 2.42 (s, 3H, H-14); 1.95-1.54 (m, [20H], CH2 of PCy3); 1.30-1.23 (m, [20H], CH2 of PCy3). 13C NMR: 292.8 (b.s, C-15); 170.5 (s, C-1); 165.3 (s, C-7); 154.3(s, C-8); 140.9 (s, C-18); 139.6 (s, C-17); 136.6 (d, C-16); 136.0 (s, C-2); 133.5 (s, C-4); 131.8 (s, C-23); 131.2 (s, C-13); 130.4 (s, C-13); 129.4 (s, C-12); 129.1 (s, C-19); 129.0 (s, C-26); 128.9 (C-9-11); 128.9 (s, C-21); 128.2 (s, C-22); 128.0 (s, C-27); 127.4 (s, C-24); 126.3 (s, C-25); 125.5 (C-9-11); 124.7 (s, C-20); 122.4 (s, C-5); 117.5 (s, C-6); 117.3 (C-9-11); 114.4 (s, C-3); 33.1 (s, C-14); cyclohexyl resonances: 33.1 (d, J = 19.7 Hz); 29.8 (s); 29.3 (s) ; 27.8 (dd, J1 = 30 Hz, J1 = 10 Hz); 26.6 (dd, J1 = 82 Hz, J1 = 11 Hz); 26.5 (s). 31P NMR: 37.24 ppm (broad singlet)

References: [1]Patent: US2011/65925,2011,A1 .Location in patent: Page/Page column 9.
[2]Patent: EP2151445,2010,A1 .Location in patent: Page/Page column 16; 17.
[3]Patent: EP2151446,2010,A1 .Location in patent: Page/Page column 17.

7
[ 250220-36-1 ]
[ 874161-53-2 ]
(1-mesityl-3-methyl-2H-4,5-dihydroimidazol-2-ylidene)(tricyclohexylphosphine)-3-phenyl-1H-inden-1-ylidene ruthenium (II) dichloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With potassium 2-methylbutan-2-olate; In hexanes; at 50℃; for 12h;	Synthesis of Catalyst 1: (1-mesityl-3-methyl-2H-4,5-dihydroimidazol-2-ylidene)(tricyclohexylphosphine)-3-phenyl-1H-inden-1-ylideneruthenium(II) dichloride To a solution of Compound B (50 mg, 0.172 mmol) in 5 mL hexanes was added potassium tert-pentoxide (KOtPn) (0.172 mmol) from a 15% solution in hexanes. To this solution was added bis(tricyclohexylphosphine)-3-phenyl-1H-inden-1-ylideneruthenium (II) dichloride (purchased from Strem Chemicals, (Newburyport, Mass.)) (145 mg, 0.156 mmol) and the solution then stirred for 12 hours at 50 C. After cooling to room temperature, the solution was concentrated to approximately 2 mL under a stream of nitrogen, then filtered and washed with hexanes, yielding 105 mg (79%) of Catalyst 1 as a brown powder.

References: [1]Patent: US2011/112302,2011,A1 .Location in patent: Page/Page column 15; 16.

8
[ 116-17-6 ]
[ 250220-36-1 ]
C₄₂H₆₄Cl₂O₃P₂Ru [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	In dichloromethane; at 20℃; for 24h;Inert atmosphere;	Under an inert atmosphere, tnisopropylphosphite (364 μΙ_, 1.53 mmol) was added to a solution of M1 (1.4145 g, 1.53 mmol), in dichloromethane (20 mL). The mixture was stirred for 24h at room temperature, then the solvent was removed in vacuo. The crude was recrystallised from CH2CI2/pentane. The solid was collected by filtration and washed with pentane (3 x 10, 2 x 15 mL). The product 68 was obtained as a brownish red solid (1.116 g, 85% yield).1H-NMR (400 MHz, 298K): 5 (ppm) = 1.10-1.35 (m, 27 H), 1.40-1.55 (m, 6 H), 1.60- 1.85 (m, 14H), 6.79 (s, 1 H, indenylidene H), 7.27 (d, J = 7.1 Hz, 1 H, indenylidene H), 7.43 (dd, J = 6.7 Hz, J = 6.3 Hz, 1 H, indenylidene), 7.44 (dd, J = 7.4 Hz, J = 6.3 Hz, 2H, indenylidene), 7.50 (dd, J = 7.4 Hz, J = 7.7 Hz, 1 H, indenylidene), 7.53 (dd, J = 7.4 Hz, J = 7.4 Hz, 1 H, indenylidene), 7.76 (d, 3JHH = 7.3 Hz, 2H, indenylidene), 8.80 (d, J = 7.3 Hz, 1 H, indenylidene).^P- - MR (162 MHz, 298K): δ (ppm) 120.1 (d, J= 37.0 Hz), 47.4 (d, J= 37.0 Hz).

References: [1]Patent: WO2011/117571,2011,A1 .Location in patent: Page/Page column 34-35.

9
[ 250220-36-1 ]
[ 1374958-02-7 ]
[RuCl₂(C₃H₄N₂(C₆H(CH₂CH₂CH₂)2)2)(PCy₃)(3-phenylindenylid-1-ene)] [ No CAS ]

References: [1]Journal of Organometallic Chemistry,2012,vol. 710,p. 68 - 74.

10
[ 250220-36-1 ]
[ 250285-32-6 ]
RuCl₂(C₉H₅Ph)(tricyclohexylphosphine)(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene) [ No CAS ]

References: [1]Chemistry - A European Journal,2012,vol. 18,p. 12845 - 12853.

11
[ 250220-36-1 ]
[ 250285-32-6 ]
[(IPr)(py)RuCl₂(3-phenylindenylid-1-ene)] [ No CAS ]

References: [1]Chemistry - A European Journal,2012,vol. 18,p. 12845 - 12853.

12
1,3-di-o-tolyl-4,5-dihydro-3H-imidazolium chloride [ No CAS ]
[ 250220-36-1 ]
[(oTol)RuCl₂(PCy₃) (Ind)] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With potassium hexamethylsilazane; In toluene; at 20℃; for 1h;Inert atmosphere; Schlenk technique;	Using protective argon atmosphere, 500 mg (0.542 mmol) of the solid (pre)catalyst (Ml) were placed in the Schlenk flask 1, followed by adding dry, deoxygenated toluene (40ml). Using protective argon atmosphere, 374 mg (1.3 mmol,2.4 equiv.) of 1,3-di-o-tolyl-4,5-dihydro-3H-imidazole chloride (the NHC salt) were placed in the Schlenk flask 2, followed by adding a KHMDS solution (1.73 mmol, 3.2 equiv.) in dry, deoxygenated toluene (10 ml). The reaction mixture was stirred at room temperature for 1-5 minutes,and then the so-obtained clear solution of free carbene was transferred via cannula to the Schlenk flask 1, using argon overpressure. The resulting reaction mixture was stirred at room temperature for 1 hour. From that momenton, all further operations were carried out without using protective argon atmosphere. The reaction mixture was concentrated in vacuo at a temperature of 30C, and the obtained residue (10 ml) was chromatographed over silica gel, using 4% of ethyl acetate in cyclohexane as an eluent.Then the solvents were evaporated in vacuo at a temperature of 30C, to yield the product as a film. n-Pentane was added to the purified product (5 ml), the resulting suspension was placed in an ultrasound bath for 5 minutes. The precipitated product was filtered off, washed withpentane (2x5 ml) and dried in vacuo, to afford the (pre)catalyst [(oTol)RuC12(PCy3) (md)] (2) as a brown-red solid (257 mg, 53%). ‘H NMR (200 MHz, CDCl3) : 6 8.70 -8.25 (m, 2H), 7.60 (t, 3J(H,H) 6.8 Hz, 2H), 7.50 -7.25 (m, 6H), 7.20 - 6.20 (m, 8H), 4.45 - 4.05 (m, 2H), 4.02 - 3.50 (m,2H), 2.77 - 2.52 (m, 3H), 2.17 - 1.98 (m, 3H), 1.95 - 1.68(bs, 3H), 1.67 - 0.57 (m, 30H). ‘3C NMR (125 MHz, CDC13) : 6301.5, 222.3, 213.4 (d), 171.1, 160.5 (d), 147.3, 145.9,145.5, 142.8, 141.1, 140.9, 140.3, 139.7, 139.1, 138.0,137.8, 137.1, 136.6, 135.2, 134.5, 134.1, 131.7, 131.6,131.0, 129.8, 129.4, 129.1, 128.8, 128.8, 128.6, 128.4,128.2, 127.9, 127.7, 127.5, 126.6, 126.4, 126.1, 125.8,124.9, 123.9, 123.8, 122.7, 117.8, 117.5, 116.6, 116.4,103.0, 95.9, 92.7, 57.8, 53.2, 53.2, 51.1, 46.0, 38.2,38.1, 34.1, 34.0, 33.8, 33.8, 30.6, 30.3, 29.1, 29.0, 28.8,27.9, 27.8, 27.7, 27.6, 27.5, 26.8, 26.3, 26.2, 25.4, 22.3,19.7, 19.6, 19.0, 18.4, 14.0. 3’P NMR (80 MHz, toluene-d8)6 21.4, 21.3, 19.1, 15.9. IR (KBr) : 3436 w, 3052 w, 2923 ss, 2847 s, 1494 s, 1438 s, 1425 s, 1270 s, 755 s, 735 m, 721 m, 697 m. Elemental analysis for C50H61N2C12PRu:calculated: C, 67.25; H, 6.89; N, 3.14; Cl 7.94. Found: C, 67.33; H, 6.90; N, 3.03; Cl, 7.91.

References: [1]Chemical Communications,2013,vol. 49,p. 3188 - 3190.
[2]Patent: WO2014/27040,2014,A1 .Location in patent: Page/Page column 16-18.

15
[ 250220-36-1 ]
[ 67191-35-9 ]
dichloro(o-isopropoxyphenylmethylene)(tricyclohexylphosphine)ruthenium(II) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With Amberlyst 15-A resin; In dichloromethane; at 40℃; for 1.25h;Inert atmosphere;	A flame-dried Schlenk reaction flask is charged with a stir bar and put under an Ar atmosphere. 923 mg [Dichloro-(3-phenyl-1H-inden-1-ylidene)-bis-(tricyclohexyl-phosphine)-ruthenium(II)] 2a (1.0 mmol; Umicore AG & Co KG, Hanau), 173 mg 2-isopropoxystyrene (1.05 mmol; 1.05 equiv.; Aldrich) and 1026 mg Amberlyst 15-A resin in dry form (4.0 mmol, 4 equiv.; Rohm and Haas Co., Philadelphia, USA) are loaded into the reaction flask and 25 mL dichloromethane (DCM) is added. The reaction is stirred at 40 C. for 75 minutes and the solution colored from red to brown. Subsequently, the reaction mixture is sent through a Pasteur pipette equipped with a cotton plug to remove the Amberlyst resin. Evaporation of all volatiles, suspending the residue in 20 mL n-hexane and subsequent filtration and drying of the precipitate in vacuo afforded 548 mg of the desired compound 3a (yield: 91%)
74%	With copper chloride (I); In dichloromethane; at 40℃; for 2h;Schlenk technique; Inert atmosphere;	In an oven dried Schlenk under Ar, were placed Dichloro(3-phenyl-1 H-inden-1 -ylidene) bis(tricyclohexylphosphine)ruthenium(ll) (M1 , HG1 Chemical Formula: C28H45CI2OPRU purchased from Umicore) complex (2.0 g, 2.2 mmol, 1 Molecular Weight: 600,61 equiv) and CuCI (236.0 mg, 2.4 mmol, 1.1 equiv). A solution of 2- isopropoxystyrene (synthesized from salicylaldehyde by alkylation and Wittig olefination following a previously reported procedure)1 (390.0 mg, 2.4 mmol, 1.1 equiv) in DCM (6 ml.) was added, then DCM was added to obtain 50 ml. solution. The resulting mixture was stirred for 2 h at 40C. The reaction was monitored by TLC (Pentane:Acetone 9:1) until the complete disappearance of M1. DCM was evaporated under reduced pressure and the solid was taken in Acetone (HPLC grade) and filtered through celite pad until the undesired solid became whitish. Volatiles were removed under vacuum and the obtained solid was dissolved in CHCI3 and filtered off. The filtrate was evaporated and the solid was dissolved in warm Et20 and the catalyst was precipitated with Pentane (3 times). The mixture was filtered off and the brown solid was collected (955 mg, 74% yield). Analytical data were consistent with the previously reported data.
73%	With copper chloride (I); In dichloromethane; at 40℃; for 2h;Inert atmosphere; Schlenk technique;	In an oven dried Schlenk under Ar, were placed Dichloro(3-phenyl-1H-inden-1-ylidene) bis(tricyclohexylphosphine)ruthenium(II) (M1, purchased from Umicore) complex (2.0 g, 2.17 mmol, 1 equiv) and CuCl (236.0 mg, 2.38 mmol, 1.1 equiv). A solution of 2-isopropoxystyrene (synthesized from salicylaldehyde by alkylation and Wittig olefination following a previously reported procedure)1 (390.0 mg, 2.40 mmol, 1.1 equiv) in DCM (6 mL) was added, then DCM was added to obtain 50 mL of solution. The resulting mixture was stirred for 2 h at 40C. The reaction was monitored by TLC (Pentane:Acetone 9:1) until the complete disappearance of M1. DCM was evaporated under reduced pressure and the solid was taken up in Acetone (HPLC grade) and filtered through a celite pad until the undesired solid became whitish. Volatiles were removed under vacuum and the solid obtained was dissolved in CHCl3 and filtered off. The filtrate was evaporated, the solid was dissolved in warm Et2O and the complex was precipitated with Pentane (3 times). The mixture was filtered off and the brown solid was collected (955 mg, 73% yield).

References: [1]Patent: US2013/35494,2013,A1 .Location in patent: Paragraph 0069; 0070.
[2]Patent: WO2022/8679,2022,A1 .Location in patent: Page/Page column 32.
[3]Journal of the American Chemical Society,2020,vol. 142,p. 19895 - 19901.
[4]Patent: WO2022/8656,2022,A1 .Location in patent: Page/Page column 37.

16
[ 1025728-53-3 ]
[ 250220-36-1 ]
copper(l) chloride [ No CAS ]
C₃₀H₄₅Cl₂F₃NO₂PRu [ No CAS ]

References: [1]European Journal of Organic Chemistry,2013,p. 8265 - 8278.

17
dichloro(3-phenyl-1H-indene-1-ylidene)(bistriphenylphosphine)ruthenium(II) [ No CAS ]
[ 2622-14-2 ]
[ 250220-36-1 ]

Yield	Reaction Conditions	Operation in experiment
88%	In tetrahydrofuran; at 40 - 65℃; for 1h;Inert atmosphere;	EXAMPLE 2 Preparation of dichloro(3-phenyl-1H-inden-1-ylidene)bis-(tricyclohexylphosphine)ruthenium(II) (according to the invention; c = 0.5 mol/l) A one liter glass reactor with condenser and stirrer is filled with argon and thereafter with 500 ml of THF. The solvent is warmed up to 40C. Then 221.7 g (250 mmol, 1 eq.) of (PPh3)2Cl2Ru(3-phenylindenylidene) (Umicore AG & Co. KG, Hanau) and 155 g (98.1% purity, 540 mmol, 2.16 eq.) of tricyclohexylphosphine (PCy3, Aldrich) are added successively with stirring. The reaction mixture is stirred under reflux (65C) for 1 h during which time the product precipitates in form of dark red crystals.

References: [1]Patent: EP2679593,2014,A1 .Location in patent: Paragraph 0070; 0071.

18
[ 250220-36-1 ]
[ 1066-54-2 ]
C₅₃H₇₈Cl₂P₂Ru [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With water; In dichloromethane-d2; for 1h;Inert atmosphere; Schlenk technique; Reflux;	Schlenk flask (20mL) equipped with a condenser and side arm closed with septa was charged under argon with [RuCl2(PCy3)2(3-phenyl-1H-inden-1-ylidene)] (10) (0.1g, 1.08×10-4mol), 6mL of methylene chloride, 77μL of ethynyltrimethylsilane (5.40×10-4mol) and 8.0μL (4.32×10-4mol) of deoxygenated water. The mixture was heated and stirred at reflux for 1h. Then the solvent was evaporated and 2mL of cold acetone (-30C) was added. The precipitate was filtered off, washed (2×2mL) with acetone (-30C), (2×2mL) with pentane (-50C) and dried in vacuum. Orange microcrystalline solid was obtained 87.0mg (84% yield).

References: [1]Journal of Organometallic Chemistry,2014,vol. 752,p. 109 - 114.

19
[ 250220-36-1 ]
[ 40935-25-9 ]

References: [1]Chemical Communications,2014,vol. 50,p. 2205 - 2207.
[2]Angewandte Chemie - International Edition,2014,vol. 53,p. 8995 - 8999.
Angew. Chem.,2014,vol. 126,p. 9141 - 9145,5.

20
[ 250220-36-1 ]
[ 1565759-33-2 ]
[(IMoTol)RuCl₂(PCy₃) (Ind)] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%		Using protective argon atmosphere, a solution of potassium tert-pentanolate (1.7 M in toluene, 0.89 ml, 1.52 mmol) was added to a suspension of 510 mg (1.52 mmol) of 1,3-di-o-tolyl-4,5-dihydro-3fi-imidazole tetrafluoroborane (the NHC salt) in dry and deoxygenated n-hexane (20 ml) in a flask. The contents of the flask was stirred at room temperature for 20 minutes. After adding 1.0 g (1.08 mmol) of the (pre ) catalyst (Ml), the reaction mixture was heated for 15 minutes at reflux. After cooling to room temperature (from that moment on, all further operations were carried out without using protective argon atmosphere), the solvent was removed in vacuo, and the residue was chromatographed over silica gel, using 20% of ethyl acetate in cyclohexane as an eluent. Then the solvents were distilled off in vacuo and the product was washed with n-pentane to afford the (pre) catalyst [ ( IMoTol) RuCl2 (PCy3) (Ind) ](5) (0.73 g, 76%) in the form of dark-red solid. 1H NMR (500 MHz, CDCl3) δ: 8.48-8.21 (m, 2H) , 7.71-6.57 (m, 18H) , 2.67-2.61 (m, 3H) , 2.07-1.99 (m, 3H) , 1.86-0.78 (m, 33H) . 13C NMR (75.4 MHz, CDCl3) δ: 142.6, 141.8, 140.7, 139.1, 138.7, 138.4, 138.2, 137.9 (d), 136.7, 136.6, 134.1, 133.2, 131.5, 130.4, 129.7, 129.6, 129.4, 129.3, 129.0, 128.8, 128.7, 128.3, 128.2, 128.1, 128.0, 127.6, 127.4, 127.3, 127.2, 126.4, 126.3, 125.5, 124.4, 123.7, 123.5, 122.7, 116.7, 116.6, 34.2, 34.1, 33.8, 33.7, 29.3, 29.2, 28.9 (d) , 27.9 (d) , 27.8, 27.7, 27.6, 27.5, 27.4, 26.9, 26.8, 26.4, 26.3, 25.6, 22.3, 19.2, 18.9, 18.3, 14.1.

References: [1]Patent: WO2014/27040,2014,A1 .Location in patent: Page/Page column 20; 21.

21
[ 250220-36-1 ]
1,3-di-(2,5-di-methylphenyl)-4,5-dihydro-3H-imidazole tetrafluoroborate [ No CAS ]
[(pXyl)RuCl₂(PCy₃) (Ind)] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%		Using protective argon atmosphere, a solution of potassium tert-pentanolate (1.7 M in toluene, 0.3 ml, 0.51 mmol) was added to a suspension of 181 mg (0.5 mmol) of l,3-di-(2,5- di-methylphenyl ) -4, 5-dihydro-3fi-imidazole tetrafluoroborate (the NHC salt) in dry and deoxygenated n-hexane (25 ml) in a Schlenk flask. The contents of the flask was stirred at room temperature for 20 minutes. After adding 151 mg (0.165 mmol) of the (pre ) catalyst (Ml), the reaction mixture was heated for 45 minutes at reflux. After cooling to room temperature (from that moment on, all further operations were carried out without using protective argon atmo sphere) , the solvent was removed in vacuo, and the residue was chromatographed over silica gel, using 5% of ethyl acetate in cyclohexane as an eluent. Then the solvents were removed in vacuo to yield the product as a film, which was dissolved in n-hexane (15 ml) and sublimation drying was carried out to afford the (pre)catalyst [(pXyl)RuCl2 (PCy3) (Ind)] (6) (72 mg, 48%) in the form of dark-red solid. 1H NMR (500 MHz, CDCl3) δ: 8.67-7.85 (m, 1H) 7.80-6.25 (m, 15H), 4.60-3.30 (m, 4H) , 3.00-0.22 (m, 45H) .

References: [1]Patent: WO2014/27040,2014,A1 .Location in patent: Page/Page column 21; 22.

22
1,3-di-o-tolyl-4,5-dihydro-3H-imidazolium chloride [ No CAS ]
[ 250220-36-1 ]
[(oTol)RuCl₂(Py) (Ind)] [ No CAS ]

References: [1]Patent: WO2014/27040,2014,A1 .

23
[ 250220-36-1 ]
1H-2-(2,4,6-trimethylphenyl)-3,4-dihydro-5-cyclopentyl-imidazolin-1-ium tetrafluoroborate [ No CAS ]
dichloro-(2-mesityl-5-cyclopentyl-3,4-dihydroimidazol-1-ylidene)-(3-phenyl-1H-inden-1-ylidene)tricyclohexylphosphine ruthenium(II) [ No CAS ]

References: [1]Dalton Transactions,2014,vol. 43,p. 7044 - 7049.

24
[ 250220-36-1 ]
1H-2-(2,4,6-trimethylphenyl)-3,4-dihydro-5-cyclododecyl-imidazolin-1-iumtetrafluoroborate [ No CAS ]
dichloro-(2-mesityl-5-cyclododecyl-3,4-dihydroimidazol-1-ylidene)-(3-phenyl-1H-inden-1-ylidene)tricyclohexylphosphine ruthenium(II) [ No CAS ]

References: [1]Dalton Transactions,2014,vol. 43,p. 7044 - 7049.

25
[ 250220-36-1 ]
2-mesityl-5-cyclopentyl-imidazolium tetrafluoroborate [ No CAS ]
dichloro-(2-mesityl-5-cyclopentyl-imidazo-1-ylidene)-(3-phenyl-1H-inden-1-ylidene)tricyclohexylphospine ruthenium (II) [ No CAS ]

References: [1]Dalton Transactions,2014,vol. 43,p. 7044 - 7049.

26
[ 250220-36-1 ]
2-mesityl-5-cyclododecyl-imidazolium tetrafluoroborate [ No CAS ]
dichloro-(2-mesityl-5-cyclododecyl-imidazo-1-ylidene)-(3-phenyl-1H-inden-1-ylidene)(tricyclohexylphospine) ruthenium (II) [ No CAS ]

References: [1]Dalton Transactions,2014,vol. 43,p. 7044 - 7049.

27
[ 250220-36-1 ]
[ 1196725-42-4 ]
[1-(2,4,6-trimethylphenyl)-3-(benzyl)-2-imidazolidinylidene]-dichloro(3-phenyl-1H-inden-1-ylidene)(tricyclohexylphosphine)-ruthenium(II) [ No CAS ]