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Chelation‐Assisted β‐Selective Direct C−H Bond Arylation of 2‐Thienylthioamide Catalyzed by Palladium–1,10‐Phenanthroline Complexes
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.201800160
Subject(s) - chemistry , palladium , chelation , catalysis , phenanthroline , reactivity (psychology) , stoichiometry , combinatorial chemistry , medicinal chemistry , polymer chemistry , organic chemistry , medicine , alternative medicine , pathology
A palladium–1,10‐phenanthroline‐catalyzed chelation‐assisted β‐selective direct C−H bond arylation of thienylthioamide was developed. The base used critically affected the reactivity: a β‐selective (3‐selective) reaction took place with K 2 CO 3 , and both the α‐ and β‐positions were arylated to give 3,5‐diarylated product with the use of Cs 2 CO 3 . The chelation‐assisted palladation affording palladacycles was confirmed by stoichiometric reactions of thienylthioamide and the catalyst precursor.