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One‐Step Synthesis of Acylboron Compounds via Copper‐Catalyzed Carbonylative Borylation of Alkyl Halides **
Author(s) -
Cheng LiJie,
Zhao Siling,
Mankad Neal P.
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202012373
Subject(s) - chemistry , halide , carbonylation , alkyl , borylation , catalysis , copper , combinatorial chemistry , organic chemistry , potassium , medicinal chemistry , aryl , carbon monoxide
A copper‐catalyzed carbonylative borylation of unactivated alkyl halides has been developed, enabling efficient synthesis of aliphatic potassium acyltrifluoroborates (KATs) in high yields by treating the in situ formed tetracoordinated acylboron intermediates with aqueous KHF 2 . A variety of functional groups are tolerated under the mild reaction conditions, and primary, secondary, and tertiary alkyl halides are all applicable. In addition, this method also provides facile access to N ‐methyliminodiacetyl (MIDA) acylboronates as well as α‐methylated potassium acyltrifluoroborates in a one‐pot manner. Mechanistic studies indicate a radical atom transfer carbonylation (ATC) mechanism to form acyl halide intermediates that are subsequently borylated by (NHC)CuBpin.