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Issue 9, 2011
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Nickel-catalyzed amination of aryl carbamates and sequential site-selective cross-couplings

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Abstract

We report the amination of aryl carbamates using nickel-catalysis. The methodology is broad in scope with respect to both coupling partners and delivers aminated products in synthetically useful yields. Computational studies provide the full catalytic cycle of this transformation, and suggest that reductive elimination is the rate-determining step. Given that carbamates are easy to prepare, robust, inert to Pd-catalysis, and useful for arene functionalization, these substrates are particularly attractive partners for use in synthesis. The sequential use of carbamate functionalization/site-selective cross-coupling processes highlights the utility of this methodology.

Graphical abstract: Nickel-catalyzed amination of aryl carbamates and sequential site-selective cross-couplings

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Publication details

The article was received on 08 Apr 2011, accepted on 12 May 2011 and first published on 09 Jun 2011


Article type: Edge Article
DOI: 10.1039/C1SC00230A
Chem. Sci., 2011,2, 1766-1771

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    Nickel-catalyzed amination of aryl carbamates and sequential site-selective cross-couplings

    T. Mesganaw, A. L. Silberstein, S. D. Ramgren, N. F. F. Nathel, X. Hong, P. Liu and N. K. Garg, Chem. Sci., 2011, 2, 1766
    DOI: 10.1039/C1SC00230A

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