Diphenyl Diselenide-Assisted Radical Addition Reaction of Diphenyl Disulfide to Unsaturated Bonds upon Photoirradiation
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Published:2023-03-07
Issue:6
Volume:28
Page:2450
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ISSN:1420-3049
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Container-title:Molecules
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language:en
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Short-container-title:Molecules
Author:
Yamamoto Yuki1ORCID,
Chen Qiqi2,
Ogawa Akiya12
Affiliation:
1. Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, Osaka 599-8531, Japan
2. Department of Applied Chemistry, Graduate School of Engineering, Osaka Metropolitan University, Osaka 599-8531, Japan
Abstract
The addition reaction of interelement compounds with heteroatom–heteroatom single bonds to unsaturated bonds under photoirradiation is an important method for the efficient and atom-economical construction of carbon–heteroatom bonds. However, in practice, the desired addition reaction is sometimes unable to proceed as expected due to the low efficiency of the desired addition reactions or the preferential polymerization of unsaturated compounds. In this study, by combining an interelement compound with homologous heteroatom compounds as a catalyst, we succeeded in suppressing the polymerization of the unsaturated compounds and in attaining a highly selective carbon–heteroatom bond formation through the desired addition reaction. In this paper, we have examined in detail whether such a “catalytic radical reaction” proceeds for unsaturated compounds and found that the dithiolation of some unsaturated compounds (i.e., vinylic ethers, styrenes, and isocyanides) could proceed with the assistance of (PhSe)2 under light. The developed methods in this study are expected to have strong implications in the fields of radical chemistry, heteroatom chemistry, synthetic organic chemistry, and catalyst chemistry as atom-economical methods for carbon–heteroatom bond formation.
Funder
JSPS KAKENHI
Ministry of Education, Culture, Sports, Science, and Technology, Japan
Nanotechnology Platform Program of the Nara Institute of Science and Technology
Subject
Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science
Cited by
1 articles.
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