1402076-72-5Relevant articles and documents
Catalyst-controlled regioselectivity in the synthesis of branched conjugated dienes via aerobic oxidative heck reactions
Zheng, Changwu,Wang, Dian,Stahl, Shannon S.
, p. 16496 - 16499,4 (2012)
Pd-catalyzed aerobic oxidative coupling of vinylboronic acids and electronically unbiased alkyl olefins provides regioselective access to 1,3-disubstituted conjugated dienes. Catalyst-controlled regioselectivity is achieved by using 2,9-dimethylphenanthroline as a ligand. The observed regioselectivity is opposite to that observed from a traditional (nonoxidative) Heck reaction between a vinyl bromide and an alkene. DFT computational studies reveal that steric effects of the 2,9-dimethylphenanthroline ligand promote C-C bond formation at the internal position of the alkene.