Aniline carbamates: a versatile and removable motif for palladium-catalyzed directed C-H activation.

Chemistry

Department of Chemistry and FQRNT Centre for Green Chemistry and Catalysis, McGill University, 801 Sherbrooke St. West, Montréal, Québec, H3A 0B8 (Canada).

Published: September 2014

The aniline carbamate is introduced as a new removable directing group for C-H activation. Its versatility and ability as a directing group are demonstrated by its use in the ortho-arylation of a wide variety of aniline derivatives under palladium(II) catalysis, with symmetric diaryliodonium salts as aryl donors. The reaction differs from previously reported arylations in its selectivity and its mechanism, as elucidated by kinetic and isotopic experiments. The directing group can also be easily removed under a variety of conditions.

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http://dx.doi.org/10.1002/chem.201403712DOI Listing

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