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Silver‐Catalyzed Double Hydrocarbonation of 2‐Trifluoromethyl‐1,3‐Conjugated Enynes with 1,3‐Dicarbonyl Compounds: Synthesis of Ring‐Trifluoromethylated Cyclopentene
Author(s) -
Zeng Yu,
Huang Chaoqian,
Ni Peiyun,
Liu Lu,
Xiao Yuanjing,
Zhang Junliang
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.201700752
Subject(s) - chemistry , trifluoromethyl , moiety , conjugated system , ring (chemistry) , intramolecular force , catalysis , cyclopentene , alkyne , aryl , intermolecular force , stereochemistry , medicinal chemistry , organic chemistry , molecule , alkyl , polymer
An unexpected atom‐economic tandem intermolecular hydrocarbonation and intramolecular hydrocarbonation (double hydrocarbonation sequence) of 2‐trifluoromethyl‐1,3‐conjugated enynes with 1,3‐dicarbonyl compounds leading to ring‐trifluoromethylated cyclo‐pentene frameworks by combination use of AgNO 3 as a catalyst and Et 3 N as a base was developed. Enynes possessing electron‐withdrawing aryl groups on the alkyne moiety are general good candidates for present transformation.