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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 international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201310457
Subject(s) - amination , chemistry , aniline , aryl , base (topology) , picoline , catalysis , halide , medicinal chemistry , polymer chemistry , aryl halide , photochemistry , organic chemistry , pyridine , palladium , 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.