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Issue 10, 2017
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Origins of high catalyst loading in copper(I)-catalysed Ullmann–Goldberg C–N coupling reactions

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Abstract

A mechanistic investigation of Ullmann–Goldberg reactions using soluble and partially soluble bases led to the identification of various pathways for catalyst deactivation through (i) product inhibition with amine products, (ii) by-product inhibition with inorganic halide salts, and (iii) ligand exchange by soluble carboxylate bases. The reactions using partially soluble inorganic bases showed variable induction periods, which are responsible for the reproducibility issues in these reactions. Surprisingly, more finely milled Cs2CO3 resulted in a longer induction period due to the higher concentration of the deprotonated amine/amide, leading to suppressed catalytic activity. These results have significant implications on future ligand development for the Ullmann–Goldberg reaction and on the solid form of the inorganic base as an important variable with mechanistic ramifications in many catalytic reactions.

Graphical abstract: Origins of high catalyst loading in copper(i)-catalysed Ullmann–Goldberg C–N coupling reactions

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Publication details

The article was received on 28 Jun 2017, accepted on 29 Aug 2017 and first published on 29 Aug 2017


Article type: Edge Article
DOI: 10.1039/C7SC02859H
Citation: Chem. Sci., 2017,8, 7203-7210
  • Open access: Creative Commons BY license
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    Origins of high catalyst loading in copper(I)-catalysed Ullmann–Goldberg C–N coupling reactions

    G. J. Sherborne, S. Adomeit, R. Menzel, J. Rabeah, A. Brückner, M. R. Fielding, C. E. Willans and B. N. Nguyen, Chem. Sci., 2017, 8, 7203
    DOI: 10.1039/C7SC02859H

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