Issue 10, 2018
From the journal:

Organic Chemistry Frontiers

Visible-light-induced methylsulfonylation/bicyclization of C(sp3)-tethered 1,7-enynes using a DMSO/H2O system†

Min-Hua Huang,‡ab   Chi-Fan Zhu,‡ab   Chun-Lan He,b   Yi-Long Zhu,*a   Wen-Juan Hao,b   De-Cai Wang,*a   Shu-Jiang Tub  and  Bo Jiang ORCID logo *b  

* Corresponding authors

a Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, Nanjing, 210009, Jiangsu, P. R. China
E-mail: dcwang@njut.edu.cn

b School of Chemistry & Materials Science, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 221116, P. R. China
E-mail: jiangchem@jsnu.edu.cn
Fax: +86 51683500065
Tel: +86 51683500065

Abstract

A visible light photocatalytic methylsulfonylation/bicyclization of C(sp3)-tethered 1,7-enynes has been established using a dimethyl sulfoxide (DMSO)/H2O system as the methylsulfonyl source. This reaction worked readily to access a wide range of sulfone-containing benzo[a]fluoren-5-ones with one quaternary carbon centre and generally good yields through C–S bond cleavage of DMSO. The reaction mechanism was proposed based on the control experiments.

Graphical abstract: Visible-light-induced methylsulfonylation/bicyclization of C(sp3)-tethered 1,7-enynes using a DMSO/H2O system

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Article information

DOI
https://doi.org/10.1039/C8QO00098K
Article type
Research Article
Submitted
29 Jan 2018
Accepted
26 Mar 2018
First published
27 Mar 2018

Org. Chem. Front., 2018,5, 1643-1650

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Visible-light-induced methylsulfonylation/bicyclization of C(sp3)-tethered 1,7-enynes using a DMSO/H2O system

M. Huang, C. Zhu, C. He, Y. Zhu, W. Hao, D. Wang, S. Tu and B. Jiang, Org. Chem. Front., 2018, 5, 1643 DOI: 10.1039/C8QO00098K

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