Chelation-Assisted beta-Selective Direct C-H Bond Arylation of 2-Thienylthioamide Catalyzed by Palladium-1,10-Phenanthroline Complexes

A palladium-1,10-phenanthroline-catalyzed chelation-assisted beta-selective direct C-H bond arylation of thienylthioamide was developed. The base used critically affected the reactivity: a beta-selective (3-selective) reaction took place with K2CO3, and both the alpha- and beta-positions were arylat...

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Bibliographic Details
Published inAsian journal of organic chemistry Vol. 7; no. 7; pp. 1323 - 1326
Main Authors Shibahara, Fumitoshi, Asai, Yusuke, Murai, Toshiaki
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.07.2018
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
TRIARYLATED AZOLES
thiophenes
REAGENTS
THIOAMIDES
ALKYNES
thiocarbonyls
SEQUENTIAL REACTIONS
C-H activation
chelation-assisted reaction
palladium
DERIVATIVES
ORGANOLITHIUM
ACCESS
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Summary:A palladium-1,10-phenanthroline-catalyzed chelation-assisted beta-selective direct C-H bond arylation of thienylthioamide was developed. The base used critically affected the reactivity: a beta-selective (3-selective) reaction took place with K2CO3, and both the alpha- and beta-positions were arylated to give 3,5-diarylated product with the use of Cs2CO3. The chelation-assisted palladation affording palladacycles was confirmed by stoichiometric reactions of thienylthioamide and the catalyst precursor.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.201800160