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

Min Hua Huang; Chi Fan Zhu; Chun Lan He; Yi Long Zhu; Wen Juan Hao; De Cai Wang; Shu Jiang Tu; Bo Jiang

doi:10.1039/c8qo00098k

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

Min Hua Huang, Chi Fan Zhu, Chun Lan He, Yi Long Zhu, Wen Juan Hao, De Cai Wang, Shu Jiang Tu, Bo Jiang

School of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

56 Scopus citations

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.

Original language	English
Pages (from-to)	1643-1650
Number of pages	8
Journal	Organic Chemistry Frontiers
Volume	5
Issue number	10
DOIs	https://doi.org/10.1039/c8qo00098k
State	Published - 21 May 2018

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

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.",

author = "Huang, {Min Hua} and Zhu, {Chi Fan} and He, {Chun Lan} and Zhu, {Yi Long} and Hao, {Wen Juan} and Wang, {De Cai} and Tu, {Shu Jiang} and Bo Jiang",

note = "Publisher Copyright: {\textcopyright} 2018 the Partner Organisations.",

year = "2018",

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doi = "10.1039/c8qo00098k",

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T1 - Visible-light-induced methylsulfonylation/bicyclization of C(sp3)-tethered 1,7-enynes using a DMSO/H2O system

AU - Huang, Min Hua

AU - Zhu, Chi Fan

AU - He, Chun Lan

AU - Zhu, Yi Long

AU - Hao, Wen Juan

AU - Wang, De Cai

AU - Tu, Shu Jiang

AU - Jiang, Bo

PY - 2018/5/21

Y1 - 2018/5/21

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=85047110700&partnerID=8YFLogxK

U2 - 10.1039/c8qo00098k

DO - 10.1039/c8qo00098k

M3 - 文章

AN - SCOPUS:85047110700

SN - 2052-4110

VL - 5

SP - 1643

EP - 1650

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

IS - 10

ER -

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

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