Copper-Catalyzed Coupling of Triaryl- and Trialkylindium Reagents with Aryl Iodides and Bromides through Consecutive Transmetalations

Surendra Thapa, Santosh K. Gurung, Diane A. Dickie, Ramesh Giri

Research output: Contribution to journalArticle

30 Citations (Scopus)

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.

Original languageEnglish (US)
Pages (from-to)11620-11624
Number of pages5
JournalAngewandte Chemie - International Edition
Volume53
Issue number43
DOIs
StatePublished - Oct 1 2014

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Reaction intermediates
Iodides
Bromides
Functional groups
Copper
Catalysts
Substrates

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Cite this

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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.",
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Copper-Catalyzed Coupling of Triaryl- and Trialkylindium Reagents with Aryl Iodides and Bromides through Consecutive Transmetalations. / Thapa, Surendra; Gurung, Santosh K.; Dickie, Diane A.; Giri, Ramesh.

In: Angewandte Chemie - International Edition, Vol. 53, No. 43, 01.10.2014, p. 11620-11624.

Research output: Contribution to journalArticle

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