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Synthesis of α‐Trifluoromethylthiolated and α‐Thiocyanated Ketones Using Umpoled Enolates
Author(s) -
Xia Xiaowen,
Chen Bocheng,
Zeng Xiaojun,
Xu Bo
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201800968
Subject(s) - chemistry , umpolung , nucleophile , sulfur , pyridine , functional group , solvent , catalysis , organic chemistry , ketone , oxide , combinatorial chemistry , polymer
An efficient synthesis of α‐trifluoromethylthiolated and α‐thiocynated ketones via Umpolung strategy is developed. Umpoled enolates (N‐alkenoxypyridinium salts) react smoothly with readily available sulfur containing nucleophiles such as AgSCF 3 and KSCN using CH 3 CN as the solvent. N‐alkenoxypyridinium salts could be easily prepared from the gold catalyzed addition of pyridine N‐oxide to alkynes. Our simple condition offers good chemical yields and high functional group tolerance.