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Mechanism of Brønsted-Base-Mediated Borylation of Propynols: A DFT Study
Haohua Chen1, Tao Zhang1, Chunhui Shan1
1School of Chemistry and Chemical Engineering and Chongqing Key Laboratory of Theoretical and Computational Chemistry , Chongqing University , Chongqing 400030 , China.
Abstract:
DFT calculations are used to reveal the mechanism of Brønsted-base-mediated borylation of propynols. The reaction is predicted to go through a key intermediate of alkenylboronate. Therefore, the possible pathways involve two key steps, borylation and reductive dehydroxylation. The favored pathway for the generation of the alkenylboronate intermediate involves alkoxy exchange, methoxylation, electrophilic substitution, and protonation. Then, the final product is yielded by a second alkoxy exchange, intramolecular nucleophilic attack, β-methoxy elimination, and protonation.
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