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Synthesis of CF 3 ‐Substituted Olefins by Julia–Kocienski Olefination Using 2‐[(2,2,2‐Trifluoroethyl)sulfonyl]benzo[ d ]thiazole as Trifluoromethylation Agent
Author(s) -
Hafner Andreas,
Fischer Tobias S.,
Bräse Stefan
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301070
Subject(s) - chemistry , sulfone , sulfonyl , thiazole , enantioselective synthesis , substrate (aquarium) , trifluoromethylation , combinatorial chemistry , organic chemistry , stereochemistry , catalysis , trifluoromethyl , alkyl , oceanography , geology
Abstract A modified Julia–Kocienski protocol was investigated for the synthesis of CF 3 ‐substituted terminal olefins. By employing a simple one‐step procedure, aldehydes were converted into the corresponding CF 3 ‐substituted olefins using 2‐[(2,2,2‐trifluoroethyl)sulfonyl]benzo[ d ]thiazole as the trifluoromethylation agent. This sulfone was prepared on a gram scale in two steps from inexpensive and commercially available trifluoroethanol. The Julia–Kocienski olefination tolerated various functional groups, and the trifluoromethylated olefins were obtained in good yields. However, the E / Z selectivity was strongly substrate dependent, and only moderate selectivities could be achieved.