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铜催化的三芳基和三烷基铟试剂与芳基碘化物和溴化物的连续交叉偶联反应。

Copper-catalyzed coupling of triaryl- and trialkylindium reagents with aryl iodides and bromides through consecutive transmetalations.

机构信息

Department of Chemistry & Chemical Biology, University of New Mexico, Albuquerque, NM 87131 (USA) https://sites.google.com/site/rgirichemistry/home.

出版信息

Angew Chem Int Ed Engl. 2014 Oct 20;53(43):11620-4. doi: 10.1002/anie.201407586. Epub 2014 Sep 11.

DOI:10.1002/anie.201407586
PMID:25213151
Abstract

An efficient copper(I)-catalyzed coupling of triaryl and trialkylindium reagents with aryl iodides and bromides is reported. The reaction proceeds at low catalyst loadings (2 mol%) and generally only requires 0.33 equivalents of the triorganoindium reagent with respect to the aryl halide as all three organic nucleophilic moieties of the reagent are transferred to the products through consecutive transmetalations. The reaction tolerates a variety of functional groups and sterically hindered substrates. Furthermore, preliminary mechanistic studies that entailed the synthesis and characterization of potential reaction intermediates offered a glimpse of the elementary steps that constitute the catalytic cycle.

摘要

报道了一种高效的铜(I)催化三芳基和三烷基铟试剂与芳基碘化物和溴化物的偶联反应。该反应在低催化剂负载量(2 mol%)下进行,通常只需要相对于芳基卤化物使用 0.33 当量的三有机铟试剂,因为试剂的所有三个有机亲核部分都通过连续的转金属化转移到产物中。该反应可耐受多种官能团和空间位阻较大的底物。此外,涉及潜在反应中间体的合成和表征的初步机理研究提供了构成催化循环的基本步骤的一瞥。

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Beilstein J Org Chem. 2015 Dec 2;11:2400-7. doi: 10.3762/bjoc.11.261. eCollection 2015.