Contribution to the Mechanism of Copper-Catalyzed C-N and C-O Bond Formation

被引：118

作者：

Lefevre, Guillaume ^{[1
]}

Franc, Gregory ^{[1
]}

Tlili, Anis ^{[2
]}

Adamo, Carlo ^{[3
]}

Taillefer, Marc ^{[2
]}

Ciofini, Ilaria ^{[3
]}

Jutand, Anny ^{[1
]}

机构：

[1] Ecole Normale Super, Dept Chim, UMR CNRS ENS UPMC 8640, F-75231 Paris 5, France

[2] Inst Charles Gerhardt Montpellier, AM2N, ENSCM, F-34296 Montpellier 5, France

[3] Chim ParisTech, ENSCP, UMR 7575, F-75231 Paris 5, France

来源：

ORGANOMETALLICS | 2012年 / 31卷 / 22期

关键词：

ARYL HALIDES; COUPLING REACTIONS; EFFICIENT SYNTHESIS; HIGHLY EFFICIENT; MILD CONDITIONS; ARYLATION; PHENOLS; COMPLEXES; BROMIDES; IODIDES;

D O I：

10.1021/om300636f

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Copper(I) species associated with 1,10-phenanthroline are generated from copper(0) precursors by chemical oxidation by the aryl halides (via electron transfer) or from copper(II) precursors by chemical reduction by N- or O- nucleophiles in the presence of a base. The mechanism of cross-coupling reactions between ArX (X = I, Br, Cl) and N- or O-nucleophiles catalyzed by copper(I) ligated to 1,3-diketonate ligands (generated from 2-acetylcyclohexanone or 2,2,6,6-tetramethyl-3,5-heptanedione) is proposed on the basis of cyclic Voltammetry, H-1 NMR, ESI-MS, and DFT calculations. The key anionic complexes [(1,3-diketonate)Cu-I-ZR](-) (ZR = NHCy, OH, OPh) undergo oxidative additions to PhI via intermediate complexes formed by halogen bonding between PhI and the negatively charged N or O atom (Z) of [(1,3-diketonate)Cu-I-ZR](-). The reductive eliminations from the Cu-III complexes (1,3-diketonate)Cu-III(Ph)-ZR generated in the oxidative additions are always faster than the rds oxidative additions.

引用

页码：7694 / 7707

页数：14

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