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Copper-Catalyzed Borylation of Acyl Chlorides with an Alkoxy Diboron Reagent: A Facile Route to Acylboron Compounds.


ABSTRACT: Herein, the copper-catalyzed borylation of readily available acyl chlorides with bis(pinacolato)diboron, (B2 pin2 ) or bis(neopentane glycolato)diboron (B2 neop2 ) is reported, which provides stable potassium acyltrifluoroborates (KATs) in good yields from the acylboronate esters. A variety of functional groups are tolerated under the mild reaction conditions (room temperature) and substrates containing different carbon-skeletons, such as aryl, heteroaryl and primary, secondary, tertiary alkyl are applicable. Acyl N-methyliminodiacetic acid (MIDA) boronates can also been accessed by modification of the workup procedures. This process is scalable and also amenable to the late-stage conversion of carboxylic acid-containing drugs into their acylboron analogues, which have been challenging to prepare previously. A catalytic mechanism is proposed based on in situ monitoring of the reaction between p-toluoyl chloride and an NHC-copper(I) boryl complex as well as the isolation of an unusual lithium acylBpinOBpin compound as a key intermediate.

SUBMITTER: Zhang X 

PROVIDER: S-EPMC9400893 | biostudies-literature | 2022 Jul

REPOSITORIES: biostudies-literature

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Copper-Catalyzed Borylation of Acyl Chlorides with an Alkoxy Diboron Reagent: A Facile Route to Acylboron Compounds.

Zhang Xiaolei X   Friedrich Alexandra A   Marder Todd B TB  

Chemistry (Weinheim an der Bergstrasse, Germany) 20220613 42


Herein, the copper-catalyzed borylation of readily available acyl chlorides with bis(pinacolato)diboron, (B<sub>2</sub> pin<sub>2</sub> ) or bis(neopentane glycolato)diboron (B<sub>2</sub> neop<sub>2</sub> ) is reported, which provides stable potassium acyltrifluoroborates (KATs) in good yields from the acylboronate esters. A variety of functional groups are tolerated under the mild reaction conditions (room temperature) and substrates containing different carbon-skeletons, such as aryl, heteroa  ...[more]

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