Radical Esterification of Unactivated Alkenes Using Formate as Carbonyl Source

In recent years, methyl formate has received considerable attention as an ideal and green C1 building block to synthesize carboxylic esters. However, examples of a one-step route to esters with one-carbon elongation using methyl formate as a source of methoxycarbonyl radical are still rare. Herein,...

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Bibliographic Details
Published in:Journal of organic chemistry 2022-04, Vol.87 (7), p.4918-4925
Main Authors: Mu, Bing, Xia, Shiwei, Wu, Linna, Li, Jingya, Li, Zhongxian, Wang, Zechao, Wu, Junliang
Format: Article
Language:English
Subjects:
Alkenes
Catalysis
Esterification
Esters
Formates
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Summary:In recent years, methyl formate has received considerable attention as an ideal and green C1 building block to synthesize carboxylic esters. However, examples of a one-step route to esters with one-carbon elongation using methyl formate as a source of methoxycarbonyl radical are still rare. Herein, we present peroxide-induced radical carbonylation of N-(2-methylallyl)­benzamides with methyl formate as the precursor of methoxycarbonyl radical and RuCl3 as catalyst, affording a series of biologically valuable 4-[(methoxycarbonyl)­methyl]-3,4-dihydroisoquinolinones with good tolerance and insensitivity to moisture in one pot under simple and mild conditions.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c02808