Download PDF
Synlett 2005(4): 658-660  
DOI: 10.1055/s-2005-863714
LETTER
© Georg Thieme Verlag Stuttgart · New York

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

Mstilsav O. Shulyupin, Evgeniy A. Chirkov, Marina A. Kazankova*, Irina P. Beletskaya
Department of Chemistry, Moscow State University (MSU), Leninskie Gory 1, Building 3, 119992 Moscow, Russia
Fax: +7(095)9328846; e-Mail: kazank@org.chem.msu.ru;
Further Information

Publication History

Received 15 December 2004
Publication Date:
22 February 2005 (online)

    Permissions and Reprints All articles of this category

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.

Key words

cross-coupling - phosphorus - nickel - alkenylphosphines

    References

  • 1 The Chemistry of Organophosphorus Compounds   Vol. 1:  Hartley FR. Wiley; Chichester, UK: 1990.  p.191 
    Google Scholar
  • 2a Edge M. Faulds P. Kelly DG. McMahon A. Ranger GC. Turner D. Eur. Pol. J.  2001,  37:  349 
    CrossrefGoogle Scholar
  • 2b Maraval V. Laurent R. Donnadieu B. Mauzac M. Caminade A.-M. Majoral J.-P. J. Am. Chem. Soc.  2000,  122:  2499 
    CrossrefGoogle Scholar
  • Some recent references:
  • 3a Tunik SP. Koshevoy IO. Poe AJ. Norlander E. Haukka M. Pakkanen TA. J. Chem. Soc., Dalton Trans.  2003,  2457 
    CrossrefGoogle Scholar
  • 3b Grachova EV. Haukka M. Heaton BT. Nordlander E. Pakkanen TA. Podkorytov IS. Tunik SP. J. Chem. Soc., Dalton Trans.  2003,  2468 
    CrossrefGoogle Scholar
  • 3c Maitra K. Nelson JH. Polyhedron  1998,  18:  203 
    CrossrefGoogle Scholar
  • 3d Barthel-Rosa LP. Maitra K. Fischer J. Nelson JH. Organometallics  1997,  16:  1714 
    CrossrefGoogle Scholar
  • For reviews, see:
  • 4a Beletskaya IP. Kazankova MA. Russ. J. Org. Chem.  2002,  38:  1391 
    CrossrefGoogle Scholar
  • 4b Tanaka M. Top. Curr. Chem.  2004,  232:  25 
    CrossrefGoogle Scholar
  • 4c Some recent papers: Takaki M. Koshoji G. Komeyama K. Takeda M. Shishido T. Kitani A. Takehira K. J. Org. Chem.  2003,  68:  6554 
    CrossrefGoogle Scholar
  • 4d See also: Mimeau D. Gaumont A. J. Org. Chem.  2003,  68:  7016 
    CrossrefGoogle Scholar
  • 4e Jerome F. Monnier F. Lawicka H. Derien S. Dixneuf PH. Chem. Commun.  2003,  696 
    CrossrefGoogle Scholar
  • 5a The Chemistry of Organophosphorus Compounds   Vol. 1:  Hartley FR. Wiley; Chichester, UK: 1990.  p.309-401  
    Google Scholar
  • 5b The Chemistry of Organophosphorus Compounds   Vol. 1:  Hartley FR. Wiley; Chichester, UK: 1990.  p.496-499  
    Google Scholar
  • 6a Colquhoun IJ. McFarlane W. J. Chem. Soc., Dalton Trans.  1982,  1915 
    CrossrefGoogle Scholar
  • 6b Bookham JL. McFarlane W. Polyhedron  1988,  7:  239 
    CrossrefGoogle Scholar
  • For reviews see ref.4a and:
  • 7a Schwan AL. Chem. Soc. Rev.  2004,  33:  218 
    CrossrefGoogle Scholar
  • 7b Some recent papers: Gelman D. Jiang L. Buchwald SL. Org. Lett.  2003,  5:  2315 
    CrossrefGoogle Scholar
  • 7c Allen DV. Venkataraman D. J. Org. Chem.  2003,  68:  4590 
    CrossrefGoogle Scholar
  • 7d Moncarz JR. Brunker TJ. Jewett JC. Orchowski M. Glueck DS. Sommer RD. Lam K.-C. Incarvito CD. Concolino TE. Ceccarelli C. Zakharov LN. Rheingold AL. Organometallics  2003,  22:  3205 
    CrossrefGoogle Scholar
  • 7e Murata M. Buchwald SL. Tetrahedron  2004,  60:  7397 
    CrossrefGoogle Scholar
  • 8 Gilbertson SR. Fu Z. Starkey GW. Tetrahedron Lett.  1999,  40:  8509 
    CrossrefGoogle Scholar
  • 9 See ref. 7b and: Trostyanskaya IG. Titskiy DY. Anufrieva EA. Borisenko AA. Kazankova MA. Beletskaya IP. Russ. Chem. Bull.  2001,  50:  2095 
    Google Scholar
  • 10 Kazankova MA. Chirkov EA. Kochetkov AN. Efimova IV. Beletskaya IP. Tetrahedron Lett.  1999,  40:  573 
    CrossrefGoogle Scholar
  • 11 There was a report that secondary phosphines were successfully used as ligands for the Heck reaction. See: Schnyder A., Aemmer T., Indolese A. F., Pittelkow U., Studer M.; Adv. Synth. Catal.; 2002, 244: 495
  • Some recent articles:
  • 12a Vila JM. Lopez-Torres M. Fernandez A. Pereira MT. Ortigueira JM. Fernandez JJ. Inorg. Chim. Acta  2003,  342:  185 
    CrossrefGoogle Scholar
  • 12b Mosteiro R. Fernandez A. Lopez-Torres M. Vazquez-Garcia D. Suarez A. Fernandez JJ. Vila JM. New J. Chem.  2002,  26:  1425 
    CrossrefGoogle Scholar
  • 12c Higgins SJ. La Pensee A. Stuart CA. Charnock JM. J. Chem. Soc., Dalton Trans.  2001,  902 
    CrossrefGoogle Scholar
  • 12d Goli MB. Grim SO. Tetrahedron Lett.  1991,  32:  363 ; and references therein
    CrossrefGoogle Scholar
  • 13a Izod K. McFarlane W. Tyson BV. Clegg W. Harrington RW. Liddle ST. Organometallics  2003,  22:  3684 
    CrossrefGoogle Scholar
  • 13b Clegg W. Izod K. McFarlane W. O’Shaughnessy P. Organometallics  1998,  17:  5231 
    CrossrefGoogle Scholar
  • 14a Mohr F. Eisler DJ. McArdle CP. Atieh K. Jennings MC. Puddephatt RJ. J. Organomet. Chem.  2003,  670:  27 
    Google Scholar
  • 14b Hunks WJ. Lapierre J. Jenkins HA. Puddephatt RJ. J. Chem. Soc., Dalton Trans.  2002,  2885 
    Google Scholar
  • 14c McArdle CP. Van S. Jennings MC. Puddephatt RJ. J. Am. Chem. Soc.  2002,  124:  3959 
    Google Scholar
  • 14d McArdle CP. Irwin MJ. Jennings MC. Vittal JJ. Puddephatt RJ. Chem.-Eur. J.  2002,  8:  723 
    Google Scholar
  • Some recent articles:
  • 15a Chen J.-L. Zhang L.-Y. Chen Z.-N. Gao L.-B. Abe M. Sasaki Y. Inorg. Chem.  2004,  43:  1481 
    CrossrefGoogle Scholar
  • 15b Ares R. Lopez-Torres M. Fernandez A. Pereira MaT. Alberdi G. Vazquez-Garcia D. Fernandez JJ. Vila JM. J. Organomet. Chem.  2003,  665:  76 
    CrossrefGoogle Scholar
  • 15c Ares R. Lopez-Torres M. Fernandez A. Castro-Juiz S. Suarez A. Alberdi G. Fernandez JJ. Vila JM. Polyhedron  2002,  21:  2309 
    CrossrefGoogle Scholar
  • 16 Brown JM. Lucy AR. J. Organomet. Chem.  1986,  314:  241 
    CrossrefGoogle Scholar
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.