Highly Selective Palladium-Catalyzed Arene C-H Acyloxylation with Benzothiadiazole as a Modifiable Directing Group

Organic Letters
Jie GuoFengzhi Zhang

Abstract

An efficient protocol for the palladium-catalyzed direct arene C-H acyloxylation of benzothiadiazole-arene derivatives is reported for the first time. The key strategy is the employment of benzothiadiazole as a modifiable directing group. The highly selective mono- or bis-acyloxylation can be achieved by tuning the reaction conditions, affording various acyloxylated benzothiadiazole derivatives, which could offer a rational tailoring of their electronic properties and be applied in organic electronic and optoelectronic materials. Finally, by diversity-oriented modification of the benzothiadiazole directing group, the acyloxylated products can be readily converted into various valuable functionalized (hetero)biaryls.

References

May 7, 2005·Organic Letters·Marappan VelusamyKuo-Chuan Ho
Sep 9, 2005·Organic Letters·Dipannita Kalyani, Melanie S Sanford
Dec 20, 2005·Chemistry : a European Journal·Shin-ichiro KatoShuntaro Mataka
Mar 10, 2006·Organic Letters·Lopa V DesaiMelanie S Sanford
Apr 26, 2007·Journal of the American Chemical Society·Shangdong YangZhangjie Shi
Sep 11, 2008·Journal of the American Chemical Society·Lopa V DesaiMelanie S Sanford
Feb 27, 2009·Journal of the American Chemical Society·Xiaodan ZhaoVy M Dong
Apr 17, 2009·Angewandte Chemie·Miłosz PawlickiHarry L Anderson
May 15, 2009·Chemical Reviews·Denise A ColbyJonathan A Ellman
Jun 27, 2009·Organic Letters·Mamoru TobisuNaoto Chatani
Dec 4, 2009·Organic Letters·Chang-Liang SunZhang-Jie Shi
Dec 10, 2009·Angewandte Chemie·Lutz AckermannAnant R Kapdi
Jan 19, 2010·Chemical Reviews·Thomas W Lyons, Melanie S Sanford
Feb 27, 2010·Journal of the American Chemical Society·Xisheng WangJin-Quan Yu
Mar 18, 2010·Angewandte Chemie·Fengzhi Zhang, Michael F Greaney
Jun 1, 2010·Journal of the American Chemical Society·Natalia ChernyakVladimir Gevorgyan
Jul 3, 2010·Journal of the American Chemical Society·Frederic W Patureau, Frank Glorius
Aug 18, 2010·Advanced Materials·John E AnthonyXiaowei Zhan
Sep 14, 2010·Chemical Reviews·Anders HagfeldtHenrik Pettersson
Sep 28, 2010·Organic Letters·Fengzhi Zhang, Michael F Greaney
Sep 13, 2011·Journal of the American Chemical Society·Li-Yen LinKen-Tsung Wong
Mar 15, 2012·Journal of the American Chemical Society·Anton V GulevichVladimir Gevorgyan
Jun 8, 2012·Advanced Materials·Thomas S van der PollGuillermo C Bazan
Aug 24, 2012·Nature Chemistry·Zachary B HensonGuillermo C Bazan
Feb 7, 2013·Nature Communications·Jingbi YouYang Yang
Oct 9, 2013·Organic Letters·Hong-Li WangShang-Dong Yang
Nov 12, 2013·Organic Letters·Hong-Yu ZhangShang-Dong Yang
Jan 31, 2014·The Journal of Organic Chemistry·Chun-Yang HeXingang Zhang
Mar 25, 2014·Chemical Communications : Chem Comm·Heng ZhangShang-Dong Yang
Jul 2, 2014·Chemical Society Reviews·Fengzhi Zhang, David R Spring
Feb 9, 2017·Journal of the American Chemical Society·Qi-Liang YangTian-Sheng Mei
Apr 27, 2017·The Journal of Organic Chemistry·Hao XieFengzhi Zhang
Nov 18, 2017·Journal of the American Chemical Society·Nicolas SauermannLutz Ackermann

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