Premium
Aminocarbonylation of (Hetero)aryl Bromides with Ammonia and Amines using a Palladium/DalPhos Catalyst System
Author(s) -
Alsabeh Pamela G.,
Stradiotto Mark,
Neumann Helfried,
Beller Matthias
Publication year - 2012
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201200580
Subject(s) - chemistry , palladium , phosphine , aryl , catalysis , amination , ligand (biochemistry) , reagent , carbon monoxide , primary (astronomy) , ammonia , organic chemistry , carbonylation , combinatorial chemistry , medicinal chemistry , astronomy , biochemistry , alkyl , receptor , physics
Variants of the DalPhos [2‐aminophenylbisadamantyl)phosphine] ligand family were examined in a palladium‐catalyzed carbonylative amination reaction using inexpensive carbon monoxide and ammonia as reagents. As a result of this survey, the Pyr‐DalPhos ligand was identified as being effective for the selective aminocarbonylation of aryl bromides with ammonia, as well as primary and secondary alkylamines. A variety of primary aromatic, heteroaromatic and N ‐substituted benzamides were formed in moderate to good yields. As part of this study, a (Mor‐DalPhos)Pd‐benzoyl complex was prepared and crystallographically characterized, thereby showing the viability of the carbonyl insertion step.