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3‐Trifluoromethylated Coumarins and Carbostyrils by Radical Trifluoromethylation of ortho ‐Functionalized Cinnamic Esters
Author(s) -
Chaabouni Slim,
Simonet Florent,
François Alison,
Abid Souhir,
Galaup Chantal,
Chassaing Stefan
Publication year - 2017
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.201601181
Subject(s) - trifluoromethylation , chemistry , regioselectivity , reagent , furocoumarins , functional group , organic chemistry , combinatorial chemistry , trifluoromethyl , photochemistry , catalysis , alkyl , polymer
A method for the trifluoromethylation of ortho ‐hydroxycinnamic esters was developed to achieve the regioselective synthesis of 3‐trifluoromethylated coumarins. The reaction was performed by using the Togni reagent as the CF 3 source under mild conditions and showed good functional‐ group tolerance. The scope of this copper‐mediated method was further expanded to the synthesis of 3‐trifluoromethylated carbostyrils starting from ortho ‐aminocinnamic derivatives. Interestingly, a sequential one‐pot synthesis of 3‐trifluoromethylated coumarins starting from salicylaldehydes was further developed. The mechanism of this cascade reaction was explored, and a radical pathway was found to be consistent with the obtained results.