DMSO as a Switchable Alkylating Agent in Heteroarene C-H Functionalization

Chemistry : a European Journal
R Aleyda Garza-SanchezFrank Glorius

Abstract

Herein, we report a novel strategy for the activation of DMSO to act as a versatile alkylating agent in heteroarene C-H functionalization. This direct, simple, and mild switch between methylation/trideuteromethylation and methylthiomethylation of heteroarenes was achieved under reagent-controlled photoredox catalysis conditions. The proposed mechanism is supported by both experimental and computational studies.

References

Apr 1, 1967·Angewandte Chemie·D MartinH J Niclas
Sep 1, 1995·Free Radical Biology & Medicine·S HixO Augusto
Sep 2, 2009·The Journal of Physical Chemistry. B·Conor CreanVladimir Shafirovich
Jun 10, 2010·Chemical Society Reviews·Jagan M R Narayanam, Corey R J Stephenson
Jun 24, 2010·Nature Chemistry·Tehshik P YoonJuana Du
Mar 12, 2011·Organic Letters·Gary A MolanderValerie A Braz
Jun 20, 2012·Angewandte Chemie·Jun Xuan, Wen-Jing Xiao
Aug 8, 2012·Chemical Society Reviews·Lei Shi, Wujiong Xia
Mar 21, 2013·Chemical Reviews·Christopher K PrierDavid W C MacMillan
Apr 19, 2013·The Journal of Organic Chemistry·Marc PressetGary A Molander
Oct 24, 2013·Angewandte Chemie·Heike Schönherr, Tim Cernak
Mar 1, 2014·Science·Danielle M Schultz, Tehshik P Yoon
Mar 7, 2014·Chemistry : a European Journal·Matthew N HopkinsonFrank Glorius
Mar 13, 2014·Journal of the American Chemical Society·Jinghan GuiPhil S Baran
Mar 29, 2014·Angewandte Chemie·Daniel A DiroccoMatthew Tudge
Aug 27, 2015·Nature·Jian Jin, David W C MacMillan
Sep 16, 2015·Current Topics in Medicinal Chemistry·Minghao FengXuefeng Jiang
Jun 18, 2016·The Journal of Organic Chemistry·Chelsea A HuffShane W Krska
Jun 21, 2016·Chemical Communications : Chem Comm·Mukund M D Pramanik, Namrata Rastogi
Oct 7, 2016·Chemical Communications : Chem Comm·Roberta CaporasoAndrey P Antonchick
Jul 29, 2017·The Journal of Organic Chemistry·Vera P DemertzidouAlexandros L Zografos
Aug 2, 2017·Angewandte Chemie·Felix J R KlauckFrank Glorius
Nov 23, 2017·Chemical Science·T McCallumL Barriault

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Citations

Jul 31, 2019·Organic & Biomolecular Chemistry·Shaohua JiangXiuwen Chen
Mar 20, 2019·Angewandte Chemie·Rupert S J Proctor, Robert J Phipps
Jan 9, 2020·Angewandte Chemie·Jamie A LeitchDarren J Dixon
Nov 5, 2020·Angewandte Chemie·Liubov I PanferovaAlexander D Dilman
Dec 23, 2020·Chemical Society Reviews·Rolando CannalireMariateresa Giustiniano
Mar 11, 2021·Chemical Society Reviews·Daniya AynetdinovaDarren J Dixon
Jul 24, 2021·Organic Letters·Edwin Alfonzo, Sudhir M Hande
Jan 9, 2020·The Journal of Organic Chemistry·Samantha RoheLouis Barriault
May 16, 2019·The Journal of Organic Chemistry·Jianyang DongQingmin Wang

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