Experimental evidence supporting a CuIII intermediate in cross-coupling reactions of allylic esters with diallylcuprate species

Chemistry - A European Journal

Volumn 7, Issue 9, 2001, Pages 1981-1989

  Sofia, A ^b   Karlstrom E ^a   Bäckvall, Jan E ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

^b NONE

Author keywords

C C coupling; Copper; Cuprate; Organocopper(III) intermediate; Reaction mechanisms

Indexed keywords

COPPER; OLEFINS; STABILIZATION; STOICHIOMETRY;

ALLYLIC LIGANDS;

ESTERS;

COPPER DERIVATIVE; ESTER DERIVATIVE;

ARTICLE; CATALYSIS; CROSS LINKING; REACTION ANALYSIS; STOICHIOMETRY; SYNTHESIS;

EID: 0035805286     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20010504)7:9<1981::AID-CHEM1981>3.0.CO;2-C     Document Type: Article

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116. 2CuLi · LiCN. The cyano group was found not to be bound to copper, and this class of reagents was proposed to be called cyano-Gilman reagents. See for example: a) S. H. Bertz, J. Am. Chem. Soc. 1990, 112, 4031-4032; b) S. H. Bertz, J. Am. Chem. Soc. 1991, 113, 5471-5474; S. H. Bertz, G. Miao, M. Eriksson, Chem. Commun. 1996, 815-816; S. H. Bertz, K. Nilsson, Ö, Davidsson, J. P. Snyder, Angew. Chem. 1998, 110, 327-331; Angew. Chem. Int. Ed. 1998, 37, 314-317; e) C. M. P. Kronenburg, J. T. B. H. Jastrzebski, A. L. Spek, G. van Koten, J. Am. Chem. Soc. 1998, 120, 9688-9689; f) G. Boche, F. Bosold, M. Marsch, K. Harms, Angew. Chem. 1998, 110, 1779-1781; Angew. Chem. Int. Ed. 1998, 37, 1684-1686;
117. 2CuLi · LiCN. The cyano group was found not to be bound to copper, and this class of reagents was proposed to be called cyano-Gilman reagents. See for example: a) S. H. Bertz, J. Am. Chem. Soc. 1990, 112, 4031-4032; b) S. H. Bertz, J. Am. Chem. Soc. 1991, 113, 5471-5474; S. H. Bertz, G. Miao, M. Eriksson, Chem. Commun. 1996, 815-816; S. H. Bertz, K. Nilsson, Ö, Davidsson, J. P. Snyder, Angew. Chem. 1998, 110, 327-331; Angew. Chem. Int. Ed. 1998, 37, 314-317; e) C. M. P. Kronenburg, J. T. B. H. Jastrzebski, A. L. Spek, G. van Koten, J. Am. Chem. Soc. 1998, 120, 9688-9689; f) G. Boche, F. Bosold, M. Marsch, K. Harms, Angew. Chem. 1998, 110, 1779-1781; Angew. Chem. Int. Ed. 1998, 37, 1684-1686;
118. 2CuLi · LiCN. The cyano group was found not to be bound to copper, and this class of reagents was proposed to be called cyano-Gilman reagents. See for example: a) S. H. Bertz, J. Am. Chem. Soc. 1990, 112, 4031-4032; b) S. H. Bertz, J. Am. Chem. Soc. 1991, 113, 5471-5474; S. H. Bertz, G. Miao, M. Eriksson, Chem. Commun. 1996, 815-816; S. H. Bertz, K. Nilsson, Ö, Davidsson, J. P. Snyder, Angew. Chem. 1998, 110, 327-331; Angew. Chem. Int. Ed. 1998, 37, 314-317; e) C. M. P. Kronenburg, J. T. B. H. Jastrzebski, A. L. Spek, G. van Koten, J. Am. Chem. Soc. 1998, 120, 9688-9689; f) G. Boche, F. Bosold, M. Marsch, K. Harms, Angew. Chem. 1998, 110, 1779-1781; Angew. Chem. Int. Ed. 1998, 37, 1684-1686;
119. 2CuLi · LiCN. The cyano group was found not to be bound to copper, and this class of reagents was proposed to be called cyano-Gilman reagents. See for example: a) S. H. Bertz, J. Am. Chem. Soc. 1990, 112, 4031-4032; b) S. H. Bertz, J. Am. Chem. Soc. 1991, 113, 5471-5474; S. H. Bertz, G. Miao, M. Eriksson, Chem. Commun. 1996, 815-816; S. H. Bertz, K. Nilsson, Ö, Davidsson, J. P. Snyder, Angew. Chem. 1998, 110, 327-331; Angew. Chem. Int. Ed. 1998, 37, 314-317; e) C. M. P. Kronenburg, J. T. B. H. Jastrzebski, A. L. Spek, G. van Koten, J. Am. Chem. Soc. 1998, 120, 9688-9689; f) G. Boche, F. Bosold, M. Marsch, K. Harms, Angew. Chem. 1998, 110, 1779-1781; Angew. Chem. Int. Ed. 1998, 37, 1684-1686;
120. 2CuLi · LiCN. The cyano group was found not to be bound to copper, and this class of reagents was proposed to be called cyano-Gilman reagents. See for example: a) S. H. Bertz, J. Am. Chem. Soc. 1990, 112, 4031-4032; b) S. H. Bertz, J. Am. Chem. Soc. 1991, 113, 5471-5474; S. H. Bertz, G. Miao, M. Eriksson, Chem. Commun. 1996, 815-816; S. H. Bertz, K. Nilsson, Ö, Davidsson, J. P. Snyder, Angew. Chem. 1998, 110, 327-331; Angew. Chem. Int. Ed. 1998, 37, 314-317; e) C. M. P. Kronenburg, J. T. B. H. Jastrzebski, A. L. Spek, G. van Koten, J. Am. Chem. Soc. 1998, 120, 9688-9689; f) G. Boche, F. Bosold, M. Marsch, K. Harms, Angew. Chem. 1998, 110, 1779-1781; Angew. Chem. Int. Ed. 1998, 37, 1684-1686;
121. 2CuLi · LiCN. The cyano group was found not to be bound to copper, and this class of reagents was proposed to be called cyano-Gilman reagents. See for example: a) S. H. Bertz, J. Am. Chem. Soc. 1990, 112, 4031-4032; b) S. H. Bertz, J. Am. Chem. Soc. 1991, 113, 5471-5474; S. H. Bertz, G. Miao, M. Eriksson, Chem. Commun. 1996, 815-816; S. H. Bertz, K. Nilsson, Ö, Davidsson, J. P. Snyder, Angew. Chem. 1998, 110, 327-331; Angew. Chem. Int. Ed. 1998, 37, 314-317; e) C. M. P. Kronenburg, J. T. B. H. Jastrzebski, A. L. Spek, G. van Koten, J. Am. Chem. Soc. 1998, 120, 9688-9689; f) G. Boche, F. Bosold, M. Marsch, K. Harms, Angew. Chem. 1998, 110, 1779-1781; Angew. Chem. Int. Ed. 1998, 37, 1684-1686;
122. 2CuLi · LiCN. The cyano group was found not to be bound to copper, and this class of reagents was proposed to be called cyano-Gilman reagents. See for example: a) S. H. Bertz, J. Am. Chem. Soc. 1990, 112, 4031-4032; b) S. H. Bertz, J. Am. Chem. Soc. 1991, 113, 5471-5474; S. H. Bertz, G. Miao, M. Eriksson, Chem. Commun. 1996, 815-816; S. H. Bertz, K. Nilsson, Ö, Davidsson, J. P. Snyder, Angew. Chem. 1998, 110, 327-331; Angew. Chem. Int. Ed. 1998, 37, 314-317; e) C. M. P. Kronenburg, J. T. B. H. Jastrzebski, A. L. Spek, G. van Koten, J. Am. Chem. Soc. 1998, 120, 9688-9689; f) G. Boche, F. Bosold, M. Marsch, K. Harms, Angew. Chem. 1998, 110, 1779-1781; Angew. Chem. Int. Ed. 1998, 37, 1684-1686;
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