Nickel-Catalyzed Cross-Coupling of Diphenylphosphine with Vinyl Bromides and Chlorides as a Route to Diphenylvinylphosphines

Abstract

An efficient nickel-catalyzed reaction for the phosphination of vinyl bromides and chlorides was developed. The procedure uses a combination of up to 1 mol% of nickel acetylacetonate, triethylamine and dimethylformamide as a solvent. The double bond geometry of the vinyl halides was retained under the reaction conditions.

cross-coupling - phosphorus - nickel - alkenylphosphines

References

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17

General Procedure (for Compounds 1-5).
A Schlenk flask was charged with 5 mmol of alkenyl bromide, 5 mmol of Et₃N, 5 mmol of diphenylphosphine, 5 mL of DMF and 1 mol% of Ni(acac)₂. The reaction mixture was stirred for specified period at maintained temperature (Table [2] ). To this mixture 20 mL of H₂O and 20 mL of benzene were added after cooling. The benzene phase was separated, washed with 10 mL of H₂O, and dried under MgSO₄. Then, 20 mg of dimethylglyoxime were added to the benzene solution. After 1 h the solution was passed through short layer of silica gel and evaporated in vacuum. The crude product was then distilled under reduced pressure.
E -(2-Ethoxyvinyl)diphenylphosphine ( 1): yield 90%, colorless oil, bp 120-124 °C/4 Torr. ¹H NMR (400 MHz, CDCl₃): δ = 1.25-1.28 (t, 3 ), 3.82-3.88 (q, 2 ), 5.32-5.35 (d, 1 , J _HH = 14 Hz), 6.86-6.92 (dd, 1 , J _HH = 14 Hz, J _PH = 9 Hz), 7.21-7.40 (m, 10 ). ¹³C NMR (100.6 MHz, CDCl₃): δ = 14.51 (-H₃), 65.24 (-O-CH₂), 97.63, 128.01, 128.21, 132.20, 159. ³¹P{H} NMR (162.6 MHz, CDCl₃): δ = -18.0. Anal. Calcd for C ₁₆H₁₇OP (%): C, 74.99; H, 6.69. Found: C, 75.02; H, 6.52.
Z -(1-Methylpropenyl)diphenylphosphine ( 2): yield 90%, colorless oil, bp 110 °C/3 Torr. ¹H NMR (400 MHz, CDCl₃): δ = 1.72 (dt, 3 H, =(P)CH₃, J _PH = 1.0 Hz, J _HH = 7.4 Hz), 1.77 (d, 3 H, =(P)CH₃, J _PH = 6.7 Hz), 5.95 (m, -H), 7.32 (m, 10 H, C₆H₅). ¹³C NMR (100.6 MHz, CDCl₃): δ = 137.09 (d, =C-P, J _P = 32.1 Hz), 133.22 (d, C=C-P, J _P = 19.8 Hz), 136.51 (d, J _P = 10.7 Hz, ipso), 128.65 (m, ₆H₅), 15.00 (d, CH₃-C=C-P, J _P = 15.2 Hz), 15.00 [d, C=C(PPh₂)CH₃, J _P = 39.6 Hz]. ³¹P{H} NMR (162.6 MHz, CDCl₃): δ = 5.9. Anal. Calcd for C₁₆H₁₇P (%): C, 79.98; H, 7.13; P, 12.89. Found: C, 79.35; H, 6.96; P, 12.83.
General Procedure (for Compounds 6, 8, 9).
A Schlenk flask was charged with 2.5 mmol of alkenyl chloride, 8 mmol of Et₃N, 2 mmol of diphenylphosphine, 3 mL of DMF, and 2 mol% of Ni(PPh₃)₂Cl₂. The solution was stirred for specified period at maintained temperature. To this solution 20 mL of H₂O and 20 mL of benzene were added after cooling. The benzene phase was separated, washed with 10 mL of H₂O and dried under MgSO₄. Then, 20 mg of dimethylglyoxime were added to benzene solution and after 1 h the solution was passed through short layer of silica gel and evaporated in vacuum. The crude product was then purified by column chromatography (Al₂O₃, THF).
1,1-Bis(diphenylphosphino)-2-( p -methoxyphenyl)ethane ( 8): yield 93%, mp 127 °C. ¹H NMR (400 MHz, CDCl₃): δ = 3.68 (s, 3 ), 6.74 (d, 1 H), 7.03-7.39 (m, 25 ). ¹³C NMR (100.6 MHz, CDCl₃): δ = 55.10 (d, O-CH₃, J = 9.0 Hz), 113.25 (d, J = 4.5 Hz), 127.68, 128.27 (dd), 130.0 (t), 131.29 (t), 132.39 [dd, Ph₂P-C(PPh₂)=C, J = 33.6 Hz, J = 48.8 Hz], 133.83 (d, J = 21.4 Hz), 134.27 (d, J = 19.8 Hz), 135.84 (dd, J = 6.1 Hz, J = 9.2 Hz), 136.47 (d, J = 15.0 Hz), 152.79 (dd, J = 9.0 Hz, J = 23.0 Hz), 159.48. ³¹P{H} NMR (162.6 MHz, CDCl₃): δ = -3.8 (d, J = 1.5 Hz), -12.0 (d, J = 1.5 Hz). Anal. Calcd for C ₃₃H₂₈P₂O (%): C, 78.80; H, 5.62. Found: C, 77.49; H, 5.79.