Visible light initiated amino group ortho-directed copper(i)-catalysed aerobic oxidative C(sp)-S coupling reaction: synthesis of substituted 2-phenylbenzothiazoles via thia-Wolff rearrangement

Chemical Communications : Chem Comm
Mandapati Bhargava Reddy, Ramasamy Anandhan

Abstract

A facile amino group ortho-directed visible-light-driven copper-catalysed aerobic oxidative C(sp)-S coupling reaction of a dimer of 2-aminothiophenol with terminal alkynes was achieved. This photochemical reaction shows an excellent conversion and chemoselectivity towards the formation of C(sp)-S coupling and has been employed for a wide range of thiol dimers, and alkynes. Furthermore, the synthetic utility of the synthesized alkynyl sulfides was demonstrated as a direct method for the construction of 2-phenylbenzothiazoles from the corresponding alkynyl sulfides via "thia-Wolff rearrangement" using AgNO3 and visible light using 9-mesityl-10-methylacridinium ions (Acr+-Mes) as photoredox catalyst system.

References

Oct 29, 2011·Angewandte Chemie·Alison E WendlandtShannon S Stahl
Mar 21, 2013·Chemical Reviews·Christopher K PrierDavid W C MacMillan
Jun 20, 2013·Journal of the American Chemical Society·Reto Frei, Jérôme Waser
Feb 12, 2014·Organic Letters·Jonathan T ReevesChris H Senanayake
Jan 8, 2015·Organic & Biomolecular Chemistry·Wen-Chieh YangChien-Tien Chen
Mar 17, 2015·Chemical Communications : Chem Comm·T HeringB König
Jul 17, 2015·Angewandte Chemie·Johannes Kaschel, Daniel B Werz
Sep 1, 2015·Organic Letters·Nieves P RamirezJose C Gonzalez-Gomez
Jun 11, 2016·Chemical Reviews·Nathan A Romero, David A Nicewicz
Aug 19, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Syed Lal Badshah, Abdul Naeem
Nov 20, 2016·Angewandte Chemie·Darryl A Boyd
Jan 31, 2018·Beilstein Journal of Organic Chemistry·Alexander Wimmer, Burkhard König
Jun 26, 2018·The Journal of Organic Chemistry·Yilmaz Kelgokmen, Metin Zora
Nov 30, 2018·Accounts of Chemical Research·Durga Prasad HariJerome Waser
May 3, 2019·Science·Asik HossainOliver Reiser

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Citations

Jun 17, 2020·Organic & Biomolecular Chemistry·Jeffrey SantandreaShawn K Collins
Jun 8, 2021·Chemical Science·Tsubasa MatsuzawaSuguru Yoshida
Jul 29, 2021·Organic & Biomolecular Chemistry·Mandapati Bhargava ReddyRamasamy Anandhan

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Methods Mentioned

BETA
Fluorescence spectroscopy
NMR

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