Synthesis of Boronic Esters from Organometallic Reagents and Bis(pinacolato)diboron

Chem Asian J. 2023 Dec 22:e202300911. doi: 10.1002/asia.202300911. Online ahead of print.ABSTRACTSynthesis of alkyl, aryl and vinyl boronic esters carrying various chiral and achiral diol protecting groups were synthesized starting from the corresponding alkyl, aryl and vinyl lithium or Grignard reagents. Good to excellent yields were obtained for a large range of substrates. The reaction can be conducted in gram scale to obtain the product over 80% yield. This method allows direct access to neopentyl, pinene and other boronic esters which are difficult to obtain by other methods using trimethoxyborane or 2-isoprpoxy pinacolboronic ester. Detailed mechanistic studies were conducted to understand the mechanism behind the formation of boronic ester starting from organometallic reagents.PMID:38131458 | DOI:10.1002/asia.202300911

Source: Chemistry, an Asian Journal - December 22, 2023 Category: Chemistry Authors: Swagata Paul Santanu Panda Source Type: research