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

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, a...

Full description

Saved in:
Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2020-05, Vol.56 (37), p.5058-5061
Main Authors: Chen, Xiao-Yue, Nie, Xiao-Xue, Wu, Yichen, Wang, Peng
Format: Article
Language:English
Subjects:
Aromatic compounds
Functional groups
Ibuprofen
NMR
Nuclear magnetic resonance
Substrates
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:1359-7345
1364-548X
DOI:10.1039/d0cc00641f