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Palladium‐Catalyzed Hydroalkynylation of Alkylidenecyclopropanes
Author(s) -
Villarino Lara,
López Fernando,
Castedo Luis,
Mascareñas José L.
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200901821
Subject(s) - catalysis , regioselectivity , alkyne , chemistry , steric effects , palladium , cleavage (geology) , bond cleavage , catalytic cycle , medicinal chemistry , combinatorial chemistry , stereochemistry , organic chemistry , materials science , fracture (geology) , composite material
Halogen‐free CC coupling : Catalytic amounts of [Pd 2 (dba) 3 ] (dba=dibenzylideneacetone) and a sterically encumbered phosphite ( L1 ) promote the addition of CH bonds of terminal alkynes ( 2 ) to alkylidenecyclopropanes ( 1 ). The reaction gives rise to 1,4‐enynes ( 3 ) in good yields. The catalytic cycle probably consists of a Pd‐catalyzed CH activation of the terminal alkyne, a regioselective hydropalladation followed by distal bond cleavage of the alkylidenecyclopropane, and a final reductive elimination.