Synthesis of Boronic Esters from Organometallic Reagents and Bis(pinacolato)diboron
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Published:2023-12-22
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Volume:
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ISSN:1861-4728
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Container-title:Chemistry – An Asian Journal
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language:en
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Short-container-title:Chemistry An Asian Journal
Author:
Paul Swagata1,
Panda Santanu2
Affiliation:
1. Indian Institute of Technology Kharagpur chemistry INDIA
2. Indian Institute of Technology Kharagpur Department of Chemistry Chemistry IIT Kharagpur, Organic chemistry building, OC-207 Near Rubber technology department 721302 Kharagpur INDIA
Abstract
Synthesis 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.
Subject
General Chemistry,Biochemistry,Organic Chemistry