Open AccessSynthesis of 4‐aryl‐ and 4‐acyl‐1,3‐dithiole‐2‐thiones via deprotonative zincation of 1,3‐dithiole‐2‐thione
Author(s) -
Otsuka Shinya,
Yorimitsu Hideki
Publication year - 2018
Publication title -
heteroatom chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.283
H-Index - 42
eISSN - 1098-1071
pISSN - 1042-7163
DOI - 10.1002/hc.21432
Subject(s) - chemistry , lithium diisopropylamide , aryl , acylation , lithium (medication) , organic chemistry , catalysis , coupling reaction , medicinal chemistry , deprotonation , ion , alkyl , medicine , endocrinology
We have developed deprotonative zincation of 1,3‐dithiole‐2‐thione at the 4‐position. Addition of lithium diisopropylamide to a THF solution of 1,3‐dithiole‐2‐thione containing ZnI 2 and LiI generated the corresponding organozinc species. After this zincation, various aryl and acyl groups were installed at the 4‐position by Pd‐catalyzed cross‐coupling reaction with aryl iodides and Cu‐catalyzed acylation with acyl chlorides, respectively.