Journal
GREEN SYNTHESIS AND CATALYSIS
Volume 2, Issue 3, Pages 275-285Publisher
KEAI PUBLISHING LTD
DOI: 10.1016/j.gresc.2021.05.001
Keywords
d2-methylenation; Homologation; DMTT; 12-Migration; Organoboron
Categories
Funding
- National Natural Science Foundation of China of China [21672097, 21972064, 21901111]
- National Natural Science Foundation of China of Jiangsu Province [BK20170632]
- Excellent Youth Foundation of Jiangsu Scientific Committee [BK20180007]
- Innovation & Entrepreneurship Talents Plan of Jiangsu Province
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An efficient method for the synthesis of deuterated homologation of boronate esters was developed using DMTT as d2-methylene source. The reaction mechanism involves base promoted deprotonation of DMTT to generate d2-sulfurmethylene ylide intermediate, which attacks the boron atom of boronic ester followed by 1,2-migration to afford the deuterated boronic homologues. This provides a unique approach to achieve one-carbon growth under practical mild conditions.
An efficient method for the synthesis of deuterated homologation of boronate esters was developed. This discovery uses robust deuterated agent 5-(methyl-d3)-5H-dibenzo[b,d]thiophen-5-ium trifluoromethane sulfonate (DMTT) as d2-methylene source. Mechanistically, base promoted deprotonation of DMTT to generate d2-sulfurmethylene ylide intermediate, which attack the boron atom of boronic ester and followed by 1,2-migration to afford the deuterated boronic homologues. The developed protocol provides a unique approach to achieve onecarbon growth under the practical mild conditions.
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