One-Step Synthesis of Acylboron Compounds via Copper-Catalyzed Carbonylative Borylation of Alkyl Halides*.
Angew Chem Int Ed Engl
; 60(4): 2094-2098, 2021 01 25.
Article
em En
| MEDLINE
| ID: mdl-33090619
ABSTRACT
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 inâ
situ formed tetracoordinated acylboron intermediates with aqueous KHF2 . 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.
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01-internacional
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MEDLINE
Idioma:
En
Ano de publicação:
2021
Tipo de documento:
Article