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Copper‐Catalyzed Cross‐Coupling of Fluorinated Vinylstannanes with Organic Halides
Author(s) -
Zine Khalid,
Petrignet Julien,
Delaye PierreOlivier,
Carcenac Yvan,
Parrain JeanLuc,
Abarbri Mohamed
Publication year - 2016
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201600024
Subject(s) - isomerization , halide , chemistry , catalysis , trifluoromethyl , aryl , medicinal chemistry , adduct , copper , palladium , double bond , coupling (piping) , polymer chemistry , organic chemistry , photochemistry , materials science , alkyl , metallurgy
β‐stannylated propenoates 2 bearing a β‐trifluoromethyl group, readily available by hydrostannation of 1 , undergo copper(I) catalyzed coupling reactions without any palladium catalyst with allyl, benzyl, alkynyl, acyl and aryl halides. The corresponding adducts were obtained in moderate to good yields with a total retention of the double bond configuration. Interestingly, allyl bromides substituted with a stabilizing group did not led to expected coupling products but to the isomerization products 3 . Thus, 31 examples are reported with yields up to 89 %. Finally, a mechanistic study was performed in order to confirm the mechanistic proposal.