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para-Selective arylation and alkenylation of monosubstituted arenes using thianthrene S-oxide as a transient mediator

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Abstract

Using thianthrene S-oxide (TTSO) as a transient mediator, para-arylation and alkenylation of mono-substituted arenes have been demonstrated via a para-selective thianthrenation/Pd-catalyzed thio-Suzuki–Miyaura coupling sequence under mild conditions. This reaction features a broad substrate scope, and functional group and heterocycle tolerance. The versatility of this approach was further demonstrated by late-stage functionalization of complex bioactive scaffolds, and direct synthesis of some pharmaceuticals, including Tetriprofen, Ibuprofen, Bifonazole, and LJ570.

Graphical abstract: para-Selective arylation and alkenylation of monosubstituted arenes using thianthrene S-oxide as a transient mediator

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Article information


Submitted
23 Jan 2020
Accepted
13 Mar 2020
First published
16 Mar 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

para-Selective arylation and alkenylation of monosubstituted arenes using thianthrene S-oxide as a transient mediator

X. Chen, X. Nie, Y. Wu and P. Wang, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC00641F

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