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Palladium‐Catalyzed Oxidative Intermolecular Difunctionalization of Terminal Alkenes with Organostannanes and Molecular Oxygen
Author(s) -
Urkalan Kaveri Balan,
Sigman Matthew S.
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200900218
Subject(s) - chemistry , palladium , transmetalation , regioselectivity , catalysis , cationic polymerization , conjugated system , medicinal chemistry , dimethylacetamide , intermolecular force , substrate (aquarium) , double bond , oxygen , combinatorial chemistry , polymer chemistry , organic chemistry , molecule , oceanography , geology , polymer , solvent
A cationic palladium complex catalyzes the title transformations, which are thought to proceed via a π‐allyl or π‐benzyl intermediate. The regioselectivity of the reaction (1,2‐ or 1,1‐difunctionalization) depends on the type of terminal double bond (conjugated or nonconjugated) in the substrate (see scheme) and appears to be controlled by the relative rates of β‐hydride elimination and transmetalation. DMA=dimethylacetamide, Tf=triflyl.