Premium
Cover Feature: Chelation‐Assisted β‐Selective Direct C−H Bond Arylation of 2‐Thienylthioamide Catalyzed by Palladium–1,10‐Phenanthroline Complexes (Asian J. Org. Chem. 7/2018)
Author(s) -
Shibahara Fumitoshi,
Asai Yusuke,
Murai Toshiaki
Publication year - 2018
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201800206
Subject(s) - chemistry , chelation , palladium , phenanthroline , catalysis , thiophene , medicinal chemistry , double bond , polymer chemistry , combinatorial chemistry , organic chemistry
A palladium–1,10‐phenanthroline‐catalyzed chelation‐assisted β‐selective direct C−H bond arylation of 2‐thienylthioamide was developed. The catalytic system preferentially cleaved the usually inert C−H bond at the β‐position (3‐position) of thiophene, even in the presence of a C−H bond at the more reactive α‐position (5‐position), thanks to a strong chelation effect of the thiocarbonyl group. The chelation‐assisted palladation affording palladacycles was confirmed by stoichiometric reactions of the thienylthioamide and the catalyst precursor. More information can be found in the Communication by Fumitoshi Shibahara, Yusuke Asai, and Toshiaki Murai on page 1323 in Issue 7, 2018 (DOI: 10.1002/ajoc.201800160).