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Room‐Temperature Amination of Deactivated Aniline and Aryl Halide Partners with Carbonate Base Using a Pd‐PEPPSI‐IPent Cl ‐ o ‐Picoline Catalyst
Author(s) -
Pompeo Matthew,
Farmer Jennifer L.,
Froese Robert D. J.,
Organ Michael G.
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201310457
Subject(s) - chemistry , amination , aniline , aryl , base (topology) , catalysis , halide , picoline , medicinal chemistry , polymer chemistry , molecule , photochemistry , organic chemistry , pyridine , mathematical analysis , alkyl , mathematics
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 °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.