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

Tehetena Mesganaw; Amanda L. Silberstein; Stephen D. Ramgren; Noah F. Fine Nathel; Xin Hong; Peng Liu; Neil K. Garg

doi:10.1039/C1SC00230A

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Chemical Science

Issue 9, 2011

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

Tehetena Mesganaw,^a Amanda L. Silberstein,^a Stephen D. Ramgren,^a Noah F. Fine Nathel,^a Xin Hong,^a Peng Liu^a and Neil K. Garg*^a

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Department of Chemistry and Biochemistry, University of California, 607 Charles Young Drive East, Box 951569, Los Angeles, USA
E-mail: neilgarg@chem.ucla.edu

Chem. Sci., 2011,2, 1766-1771

DOI: 10.1039/C1SC00230A
Received 08 Apr 2011, Accepted 12 May 2011
First published online 09 Jun 2011

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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.

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Tehetena Mesganaw
Amanda L. Silberstein
Stephen D. Ramgren
Noah F. Fine Nathel
Xin Hong
Peng Liu
Neil K. Garg

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