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Stereoselective One‐Pot Sequential Dehydrochlorination/ trans ‐Hydrofluorination Reaction of β‐Chloro‐α,β‐unsaturated Aldehydes or Ketones: Facile Access to ( Z )‐β‐Fluoro‐β‐arylenals/β‐Fluoro‐β‐arylenones
Author(s) -
Zhang Jingli,
Liu Liran,
Duan Junxin,
Gu Lianghu,
Chen Bifeng,
Sun Taolei,
Gong Yuefa
Publication year - 2017
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.201700981
Subject(s) - chemistry , synthon , stereoselectivity , reagent , nucleophile , aryl , nucleophilic addition , organic chemistry , halogenation , organic synthesis , combinatorial chemistry , catalysis , alkyl
The monofluoroalkene substructure shows a high potential as a fluorinated synthon in organic synthesis. However, control of the Z / E stereoselectivity of multi‐substituted monofluoroalkene products in one‐pot reactions still remains a challenge. An unprecedented one‐pot approach for the highly regio‐ and stereoselective preparation of functionalized ( Z )‐β‐monofluoro tri‐substituted alkenes from readily available β‐chloro‐α,β‐unsaturated aldehydes or ketones has been explored. Mechanistic studies demonstrated that the reaction is initiated by dehydrochlorination of the substrates to give alkynyl aldehydes/ketones, followed by their trans ‐hydrofluorination. It is worth mentioning that a fluorinating reagent with suitable basicity and nucleophilicity plays a key role in promoting the formation of ( Z )‐β‐fluoro‐β‐aryl tri‐substituted monofluoroalkenes.