Benzylic C(sp3 )-H bond sulfonylation of 4-methylphenols with the insertion of sulfur dioxide under photocatalysis

Chemical Communications : Chem Comm
Xinxing GongJie Wu

Abstract

Sulfonylation of the benzylic C-H bond is developed through a three-component reaction of aryldiazonium tetrafluoroborates, 4-methylphenols and sodium metabisulfite (Na2S2O5). The inorganic sulfite of sodium metabisulfite is used as the SO2 surrogate. In this transformation, benzylic C(sp3)-H bond sulfonylation is achieved in the presence of a photocatalyst under visible light. A radical pathway involving the arylsulfonyl radical and intermolecular hydrogen atom abstraction is proposed.

References

Mar 17, 2000·Science·J Drews
Aug 5, 2004·Journal of the American Chemical Society·Lopa V DesaiMelanie S Sanford
Sep 22, 2005·Journal of the American Chemical Society·Vladimir G ZaitsevOlafs Daugulis
Jun 20, 2007·Chemical Society Reviews·Ana Minatti, Kilian Muñiz
Jun 20, 2007·Chemical Society Reviews·Sherry R Chemler, Peter H Fuller
Feb 20, 2008·Chemical Communications : Chem Comm·Angelina ProkofievaFranc Meyer
Sep 10, 2008·Journal of the American Chemical Society·Song LinZhang-Jie Shi
Feb 27, 2009·Journal of the American Chemical Society·Xiaodan ZhaoVy M Dong
Jan 30, 2010·Science·Mark S Chen, M Christina White
Feb 24, 2010·Journal of the American Chemical Society·Dmitry Shabashov, Olafs Daugulis
Oct 28, 2010·Accounts of Chemical Research·James M Mayer
Mar 18, 2011·Angewandte Chemie·Timothy Newhouse, Phil S Baran
Apr 21, 2011·Chemical Society Reviews·Olivier Baudoin
Aug 16, 2011·Advanced Materials·Kazuo TakimiyaEigo Miyazaki
Nov 15, 2011·Chemical Communications : Chem Comm·Xiangyue MengChunru Wang
Sep 5, 2012·Chemical Communications : Chem Comm·Shengqing Ye, Jie Wu
Jul 16, 2013·Organic & Biomolecular Chemistry·Philippe Bisseret, Nicolas Blanchard
Jan 1, 2014·Journal of the American Chemical Society·Yoshinori Aihara, Naoto Chatani
Mar 7, 2014·Angewandte Chemie·Qing GuLutz Ackermann
Jul 11, 2014·Chemical Communications : Chem Comm·Wanfang LiXiao-Feng Wu
Jul 16, 2014·Journal of the American Chemical Society·Adam Noble, David W C MacMillan
Sep 11, 2014·Journal of the American Chemical Society·Ru-Yi ZhuJin-Quan Yu
Dec 17, 2014·Organic & Biomolecular Chemistry·Gang LiuJie Wu
Apr 9, 2015·Organic Letters·Qixue Qin, Shouyun Yu
Apr 17, 2015·The Journal of Organic Chemistry·Guangwei RongGuoqi Zhang
May 27, 2015·Organic & Biomolecular Chemistry·Vutukuri Prakash ReddyNobuaki Kambe
Sep 9, 2015·Journal of the American Chemical Society·Pan GaoZhuangzhi Shi
Sep 16, 2015·Current Topics in Medicinal Chemistry·Minghao FengXuefeng Jiang
Sep 22, 2015·Journal of the American Chemical Society·Jitan ZhangYuhong Zhang
Oct 3, 2015·Chemical Communications : Chem Comm·Hiromichi EgamiYoshitaka Hamashima
Oct 7, 2015·Chemical Communications : Chem Comm·Hong-Wen LiangYe Wei

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Citations

Oct 24, 2018·Chemical Communications : Chem Comm·Guanyinsheng QiuJie Wu
Jan 3, 2019·Chemical Communications : Chem Comm·Shengqing YeJie Wu
Feb 1, 2019·Chemical Communications : Chem Comm·Shengqing YeGuanyinsheng Qiu
Jun 4, 2019·Organic & Biomolecular Chemistry·Akshay M NairChandra M R Volla
Jan 27, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Ming Wang, Xuefeng Jiang
Jan 8, 2020·Organic Letters·Issa Yavari, Sina Shaabanzadeh
Sep 30, 2021·Chemical Reviews·Natalie Holmberg-Douglas, David A Nicewicz

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