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Free Radical Pathway Cleavage of C—O Bonds for the Synthesis of Alkylboron Compounds
Author(s) -
Lu Xi,
Zhang ZhenQi,
Yu Lu,
Zhang Ben,
Wang Bing,
Gong TianJun,
Tian ChangLin,
Xiao Bin,
Fu Yao
Publication year - 2019
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201800500
Subject(s) - chemistry , chemoselectivity , cleavage (geology) , borylation , alkyl , catalysis , bond cleavage , combinatorial chemistry , functional group , stereochemistry , organic chemistry , aryl , polymer , geotechnical engineering , fracture (geology) , engineering
Summary of main observation and conclusion We report a silver‐catalyzed borylation of alkyl tosylates, which provides a new method for the synthesis of alkylboron compounds with good functional group compatibility and excellent chemoselectivity. The present work added highly polarized alkyl tosylate C—O bonds to the fairly limited number of C—O bonds able to participate in free radical cleavage pathways. The mechanistic studies suggested that in situ ‐generated silver(0) catalytic species were the active catalytic species and played a key role in the radical pathway cleavage of C—O bonds.