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Selective Monoarylation of Primary Amines Using the Pd‐PEPPSI‐IPent Cl Precatalyst
Author(s) -
Sharif Sepideh,
Rucker Richard P.,
Chandrasoma Nalin,
Mitchell David,
Rodriguez Michael J.,
Froese Robert D. J.,
Organ Michael G.
Publication year - 2015
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.201502822
Subject(s) - chemistry , aryl , halide , amination , palladium , alkyl , primary (astronomy) , pyridine , reactivity (psychology) , catalysis , salt (chemistry) , organic chemistry , medicinal chemistry , combinatorial chemistry , medicine , physics , alternative medicine , pathology , astronomy
A single set of reaction conditions for the palladium‐catalyzed amination of a wide variety of (hetero)aryl halides using primary alkyl amines has been developed. By combining the exceptionally high reactivity of the Pd‐PEPPSI‐IPent Cl catalyst (PEPPSI=pyridine enhanced precatalyst preparation, stabilization, and initiation) with the soluble and nonaggressive sodium salt of BHT (BHT=2,6‐di‐ tert ‐butyl‐hydroxytoluene), both six‐ and five‐membered (hetero)aryl halides undergo efficient and selective amination.