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M. O. Shulyupin et al.
LETTER
(3) Some recent references: (a) Tunik, S. P.; Koshevoy, I. O.;
Poe, A. J.; Norlander, E.; Haukka, M.; Pakkanen, T. A. J.
Chem. Soc., Dalton Trans. 2003, 2457. (b) Grachova, E. V.;
Haukka, M.; Heaton, B. T.; Nordlander, E.; Pakkanen, T. A.;
Podkorytov, I. S.; Tunik, S. P. J. Chem. Soc., Dalton Trans.
2003, 2468. (c) Maitra, K.; Nelson, J. H. Polyhedron 1998,
18, 203. (d) Barthel-Rosa, L. P.; Maitra, K.; Fischer, J.;
Nelson, J. H. Organometallics 1997, 16, 1714.
(15) Some recent articles: (a) Chen, J.-L.; Zhang, L.-Y.; Chen,
Z.-N.; Gao, L.-B.; Abe, M.; Sasaki, Y. Inorg. Chem. 2004,
43, 1481. (b) Ares, R.; Lopez-Torres, M.; Fernandez, A.;
Pereira, M. a. T.; Alberdi, G.; Vazquez-Garcia, D.;
Fernandez, J. J.; Vila, J. M. J. Organomet. Chem. 2003, 665,
76. (c) Ares, R.; Lopez-Torres, M.; Fernandez, A.; Castro-
Juiz, S.; Suarez, A.; Alberdi, G.; Fernandez, J. J.; Vila, J. M.
Polyhedron 2002, 21, 2309.
(4) For reviews, see: (a) Beletskaya, I. P.; Kazankova, M. A.
Russ. J. Org. Chem. 2002, 38, 1391. (b) Tanaka, M. Top.
Curr. Chem. 2004, 232, 25. (c) Some recent papers: Takaki,
M.; Koshoji, G.; Komeyama, K.; Takeda, M.; Shishido, T.;
Kitani, A.; Takehira, K. J. Org. Chem. 2003, 68, 6554.
(d) See also: Mimeau, D.; Gaumont, A. J. Org. Chem. 2003,
68, 7016. (e) Jerome, F.; Monnier, F.; Lawicka, H.; Derien,
S.; Dixneuf, P. H. Chem. Commun. 2003, 696.
(5) (a) The Chemistry of Organophosphorus Compounds, Vol.
1; Hartley, F. R., Ed.; Wiley: Chichester, UK, 1990, 309–
401. (b) The Chemistry of Organophosphorus Compounds,
Vol. 1; Hartley, F. R., Ed.; Wiley: Chichester, UK, 1990,
496–499.
(16) Brown, J. M.; Lucy, A. R. J. Organomet. Chem. 1986, 314,
241.
(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): d = 1.25–1.28 (t, 3 ), 3.82–3.88 (q, 2 ), 5.32–5.35 (d,
1 , JHH = 14 Hz), 6.86–6.92 (dd, 1 , JHH = 14 Hz, JPH = 9 Hz),
7.21–7.40 (m, 10 ). 13C NMR (100.6 MHz, CDCl3): d =
14.51 (-H3), 65.24 (-O-CH2), 97.63, 128.01, 128.21, 132.20,
159. 31P{H} NMR (162.6 MHz, CDCl3): d = –18.0. Anal.
Calcd for C16H17OP (%): C, 74.99; H, 6.69. Found: C, 75.02;
H, 6.52.
(6) (a) Colquhoun, I. J.; McFarlane, W. J. Chem. Soc., Dalton
Trans. 1982, 1915. (b) Bookham, J. L.; McFarlane, W.
Polyhedron 1988, 7, 239.
(7) For reviews see ref.4a and: (a) Schwan, A. L. Chem. Soc.
Rev. 2004, 33, 218. (b) Some recent papers: Gelman, D.;
Jiang, L.; Buchwald, S. L. Org. Lett. 2003, 5, 2315.
(c) Allen, D. V.; Venkataraman, D. J. Org. Chem. 2003, 68,
4590. (d) Moncarz, J. R.; Brunker, T. J.; Jewett, J. C.;
Orchowski, M.; Glueck, D. S.; Sommer, R. D.; Lam, K.-C.;
Incarvito, C. D.; Concolino, T. E.; Ceccarelli, C.; Zakharov,
L. N.; Rheingold, A. L. Organometallics 2003, 22, 3205.
(e) Murata, M.; Buchwald, S. L. Tetrahedron 2004, 60,
7397.
Z-(1-Methylpropenyl)diphenylphosphine (2): yield 90%,
colorless oil, bp 110 °C/3 Torr. 1H NMR (400 MHz, CDCl3):
d = 1.72 (dt, 3 H, =(P)CH3, JPH = 1.0 Hz, JHH = 7.4 Hz), 1.77
(d, 3 H, =(P)CH3, JPH = 6.7 Hz), 5.95 (m, -H), 7.32 (m, 10 H,
C6H5). 13C NMR (100.6 MHz, CDCl3): d = 137.09 (d, =C-P,
JP = 32.1 Hz), 133.22 (d, C=C-P, JP = 19.8 Hz), 136.51 (d,
JP = 10.7 Hz, ipso), 128.65 (m, 6H5), 15.00 (d, CH3-C=C-P,
JP = 15.2 Hz), 15.00 [d, C=C(PPh2)CH3, JP = 39.6 Hz].
31P{H} NMR (162.6 MHz, CDCl3): d = 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.
(8) Gilbertson, S. R.; Fu, Z.; Starkey, G. W. Tetrahedron Lett.
1999, 40, 8509.
(9) See ref. 7b and: Trostyanskaya, I. G.; Titskiy, D. Y.;
Anufrieva, E. A.; Borisenko, A. A.; Kazankova, M. A.;
Beletskaya, I. P. Russ. Chem. Bull. 2001, 50, 2095.
(10) Kazankova, M. A.; Chirkov, E. A.; Kochetkov, A. N.;
Efimova, I. V.; Beletskaya, I. P. Tetrahedron Lett. 1999, 40,
573.
(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.
(12) Some recent articles: (a) Vila, J. M.; Lopez-Torres, M.;
Fernandez, A.; Pereira, M. T.; Ortigueira, J. M.; Fernandez,
J. J. Inorg. Chim. Acta 2003, 342, 185. (b) Mosteiro, R.;
Fernandez, A.; Lopez-Torres, M.; Vazquez-Garcia, D.;
Suarez, A.; Fernandez, J. J.; Vila, J. M. New J. Chem. 2002,
26, 1425. (c) Higgins, S. J.; La Pensee, A.; Stuart, C. A.;
Charnock, J. M. J. Chem. Soc., Dalton Trans. 2001, 902.
(d) Goli, M. B.; Grim, S. O. Tetrahedron Lett. 1991, 32, 363;
and references therein.
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):
d = 3.68 (s, 3 ), 6.74 (d, 1 H), 7.03–7.39 (m, 25 ). 13C NMR
(100.6 MHz, CDCl3): d = 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): d = –3.8 (d, J = 1.5 Hz), –12.0 (d, J = 1.5 Hz). Anal.
Calcd for C33H28P2O (%): C, 78.80; H, 5.62. Found: C,
77.49; H, 5.79.
(13) (a) Izod, K.; McFarlane, W.; Tyson, B. V.; Clegg, W.;
Harrington, R. W.; Liddle, S. T. Organometallics 2003, 22,
3684. (b) Clegg, W.; Izod, K.; McFarlane, W.;
O’Shaughnessy, P. Organometallics 1998, 17, 5231.
(14) (a) Mohr, F.; Eisler, D. J.; McArdle, C. P.; Atieh, K.;
Jennings, M. C.; Puddephatt, R. J. J. Organomet. Chem.
2003, 670, 27. (b) Hunks, W. J.; Lapierre, J.; Jenkins, H. A.;
Puddephatt, R. J. J. Chem. Soc., Dalton Trans. 2002, 2885.
(c) McArdle, C. P.; Van, S.; Jennings, M. C.; Puddephatt, R.
J. J. Am. Chem. Soc. 2002, 124, 3959. (d) McArdle, C. P.;
Irwin, M. J.; Jennings, M. C.; Vittal, J. J.; Puddephatt, R. J.
Chem.–Eur. J. 2002, 8, 723.
Synlett 2005, No. 4, 658–660 © Thieme Stuttgart · New York