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Aminocarbonylation of Aryl Halides to Produce Primary Amides by Using NH 4 HCO 3 Dually as Ammonia Surrogate and Base
Author(s) -
Wang DongLiang,
Liu Huan,
Yang Da,
Wang Peng,
Lu Yong,
Liu Ye
Publication year - 2017
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201700893
Subject(s) - chemistry , xantphos , aryl , base (topology) , ammonia , ligand (biochemistry) , primary (astronomy) , hydrolysis , medicinal chemistry , weak base , urea , halide , combinatorial chemistry , inorganic chemistry , organic chemistry , alkyl , mathematical analysis , biochemistry , receptor , mathematics , physics , astronomy
An efficient and clean protocol was developed for rapid production of primary aromatic amides by aminocarbonylation with NH 4 HCO 3 . Without addition of auxiliary base, the use of solid and cheap NH 4 HCO 3 dually as ammonia surrogate and base not only promoted aminocarbonylation over subsequent dehydration and hydrolysis of amides owing to its weak basicity, and it also made the reaction manipulation clean and simplified without the presence of stinky NH 3 or organic amines. The Xantphos ligand with relatively intensive π‐acceptor character ( 1 J 31P–77Se =758 Hz) and wide natural bite angle ( β n =111°) was found to be indispensable for the high efficiency of this reaction.