4.8 Article

Room-Temperature Amination of Deactivated Aniline and Aryl Halide Partners with Carbonate Base Using a Pd-PEPPSI-IPentCI-o-Picoline Catalyst

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 12, Pages 3223-3226

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201310457

Keywords

amination; cross-coupling; homogeneous catalysis; palladium; PEPPSI

Funding

  1. NSERC (Canada)
  2. Ontario Research Fund (ORF, Ontario)

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Current state-of-the-art protocols for the coupling of unreactive amines (e.g., electron-poor anilines) with deactivated oxidative-addition partners (e.g., electron-rich and/or hindered aryl chlorides) involve strong heating (usually >100 degrees C) and/or tert-butoxide base, and even then not all couplings are successful. The aggressive base tert-butoxide reacts with and in many instances destroys the typical functional groups that are necessary for the function of most organic molecules, such as carbonyl groups, esters, nitriles, amides, alcohols, and amines. The new catalyst described herein, Pd-PEPPSI-IPent(Cl)-o-picoline, is able to aminate profoundly deactivated coupling partners when using only carbonate base at room temperature.

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