Homeopathic Ligand-Free Palladium as a Catalyst in the Heck Reaction. A Comparison with a Palladacycle

Organic Letters - Tập 5 Số 18 - Trang 3285-3288 - 2003
André H. M. de Vries1, Jan M. C. A. Mulders1, John Mommers1, Huub J. W. Henderickx1, Johannes G. de Vries1
1DSM Pharma Chemicals-Advanced Synthesis, Catalysis & Development, P.O. Box 18, 6160 MD Geleen, The Netherlands

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Heck R. F., 1982, Org. React., 27, 345

Heck R., 1991, Comprehensive Organic Synthesis, 833, 10.1016/B978-0-08-052349-1.00110-4

Cabri W., 1995, Acc. Chem. Res., 28, 2, 10.1021/ar00049a001

Bräse S., 1998, Metal-Catalyzed Cross-Coupling Reactions, 99

(e) Beller, M.; Riermeier, T. H.; Stark, G. InTransition Metals for Organic Synthesis; Building Blocks andFine Chemicals; Beller, M., Bolm, C., Eds.; Wiley-VCH:  Weinheim, Germany, 1998; Vol 1, p 208.

Beletskaya I. P., 2000, Chem. Rev., 100, 3009, 10.1021/cr9903048

Whitcombe N. J., 2001, Tetrahedron, 57, 7449, 10.1016/S0040-4020(01)00665-2

de Vries J. G., 2001, Can. J. Chem., 79, 1086, 10.1139/v01-033

Littke A. F., 2002, Angew. Chem., Int. Ed., 41, 4176, 10.1002/1521-3773(20021115)41:22<4176::AID-ANIE4176>3.0.CO;2-U

van Strijdonck G. P. F., 1999, Eur. J. Inorg. Chem., 1073, 10.1002/(SICI)1099-0682(199907)1999:7<1073::AID-EJIC1073>3.0.CO;2-T

Stephan M. S., 1998, Angew. Chem., Int. Ed., 37, 662, 10.1002/(SICI)1521-3773(19980316)37:5<662::AID-ANIE662>3.0.CO;2-0

Stephan M. S., 2000, Chemical Industries 82, Catalysis of Organic Reactions, 379

Jeffery, 1996, Advances in Metal-Organic Chemistry, 153

Bumagin N. A., 1989, J. Organomet. Chem., 371, 397, 10.1016/0022-328X(89)85235-0

Beletskaya I. P., 1997, Pure Appl. Chem., 69, 471, 10.1351/pac199769030471

de Vries A. H. M., 2002, Adv. Synth. Catal., 344, 996, 10.1002/1615-4169(200210)344:9<996::AID-ADSC996>3.0.CO;2-J

As, 2002, Eur. J. Inorg. Chem., 1711

Reetz M. T., 1996, Tetrahedron Lett., 37, 4499, 10.1016/0040-4039(96)00924-0

Beller M., 1996, J. Organomet. Chem., 520, 257, 10.1016/0022-328X(96)06398-X

Reetz M. T., 2000, Angew. Chem., Int. Ed., 39, 165, 10.1002/(SICI)1521-3773(20000103)39:1<165::AID-ANIE165>3.0.CO;2-B

Klingelhöfer S., 1997, J. Am. Chem. Soc., 119, 10116, 10.1021/ja9714604

Ley S. V., 2002, Chem. Commun., 1134, 10.1039/b200677b

Rahim E. H., 2001, Nano Lett., 1, 501, 10.1021/nl015574w

Kogan V., 2002, Org. Lett., 4, 3529, 10.1021/ol026689p

Gürtler C., 1999, Chem. Eur. J., 11, 3107, 10.1002/(SICI)1521-3765(19991105)5:11<3107::AID-CHEM3107>3.0.CO;2-#

de Vries, A. H. M.; de Vries, J. G. WO 02/057199 to DSM nv, 2002.

The low loading of ligand-free palladium (in our examples 0.01−0.1 mol %) has been dubbed as homeopathic doses, a phrase also used by Beletskaya and Cheprakov, see ref 1f, p 3009.

Reetz, 1998, Tetrahedron Lett., 39, 8449, 10.1016/S0040-4039(98)01967-4

Andersson C.-M., 1987, J. Org. Chem., 52, 3529, 10.1021/jo00392a007

Herrmann W. A., 1995, Angew. Chem., Int. Ed. Engl., 34, 1844, 10.1002/anie.199518441

Herrmann W. A., 1997, Chem. Eur. J., 3, 1357, 10.1002/chem.19970030823

Böhm V. P. W., 2001, Chem. Eur. J., 7, 4191, 10.1002/1521-3765(20011001)7:19<4191::AID-CHEM4191>3.0.CO;2-1

Nowotny M., 2000, Chem. Commun., 1877, 10.1039/b004502k

Rocaboy C., 2002, Org. Lett., 4, 1993, 10.1021/ol025790r

Rocaboy C., 2003, New J. Chem., 27, 39, 10.1039/b208545n

Beletskaya I. P., 2001, J. Organomet. Chem., 622, 89, 10.1016/S0022-328X(00)00876-7

Albisson D. A., 1998, Tetrahedron Lett., 39, 9793, 10.1016/S0040-4039(98)02175-3

Alonso D. A., 2002, Adv. Synth. Catal., 344, 172, 10.1002/1615-4169(200202)344:2<172::AID-ADSC172>3.0.CO;2-9

Gruber A. S., 2000, Org. Lett., 2, 1287, 10.1021/ol0057277

Iyer S., 2000, Tetrahedron Lett., 41, 8981, 10.1016/S0040-4039(00)01594-X

Gibson S., 2001, J. Chem. Commun., 779, 10.1039/b100328n

Pfaltz, 2001, J. Am. Chem. Soc., 123, 1848, 10.1021/ja003191e

Amatore C., 2000, Acc. Chem. Res., 33, 314, 10.1021/ar980063a

Evans J., 2002, J. Chem. Soc., Dalton Trans., 2207, 10.1039/b200617k

The, 2003, Org. Lett., 5, 983, 10.1021/ol027337l

Mehnert C. P., 1998, J. Am. Chem. Soc., 120, 12289, 10.1021/ja971637u

Djakovitch L., 2001, J. Am. Chem. Soc., 123, 5990, 10.1021/ja001087r

Choudary B., 2002, J. Am. Chem. Soc., 124, 14127, 10.1021/ja026975w

Mori K., 2002, J. Am. Chem. Soc., 124, 11572, 10.1021/ja020444q

Biffis A., 2001, Eur. J. Inorg. Chem., 1131, 10.1002/1099-0682(200105)2001:5<1131::AID-EJIC1131>3.0.CO;2-3

Davies I. W., 2001, J. Am. Chem. Soc., 123, 10139, 10.1021/ja016877v

Köhler K., 2002, Chem. Eur. J., 8, 622, 10.1002/1521-3765(20020201)8:3<622::AID-CHEM622>3.0.CO;2-0