Palladium-catalyzed Markovnikov terminal arylalkynes hydrostannation: application to the synthesis of 1,1-diarylethylenes.
The palladium-catalyzed hydrostannation of terminal arylalkynes was achieved. The regioselectivity of the H-Sn bond addition across the triple bond was found to be controlled by an ortho substituent on the aromatic ring, whatever its electronic nature, to give exclusively alpha-branched vinylstannanes 2 in accordance with Markovnikov's rule. Subsequent Stille cross-coupling reaction of 2 with a variety of aryl halides readily provided, in moderate to good yields, a family of functionalized 1,1-diarylethylenes 1.
Hamze
Abdallah
A
Laboratoire de Chimie Therapeutique, Faculte de Pharmacie, Universite Paris-Sud, CNRS, BioCIS, UMR 8076, rue J. B. Clement, Chatenay-Malabry, F-92296, France.
Veau
Damien
D
Provot
Olivier
O
Brion
Jean-Daniel
JD
Alami
Mouâd
M
D000480:Alkynes / Q000737:chemistry*; D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D005030:Ethylenes / Q000138:chemical synthesis*; D010165:Palladium / Q000737:chemistry; D014220:Trialkyltin Compounds / Q000737:chemistry*
D000480:Alkynes; D001555:Benzene Derivatives; D005030:Ethylenes; D014220:Trialkyltin Compounds; D010165:Palladium