Premium
Stereospecific Allyl–Aryl Coupling Catalyzed by in situ Generated Palladium Nanoparticles in Water under Ambient Conditions
Author(s) -
Zhao Jingming,
Ye Jiang,
Zhang Yong Jian
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201200704
Subject(s) - chemistry , allylic rearrangement , stereospecificity , palladium , aryl , catalysis , in situ , nanoparticle , aqueous solution , coupling (piping) , combinatorial chemistry , organic chemistry , nanotechnology , alkyl , materials science , mechanical engineering , engineering
A practical process for the stereospecific cross‐coupling of secondary allylic carbonates with arylboronic acids has been developed. The reaction is catalyzed by in situ generated palladium nanoparticles (PdNPs) without any ligands and additional stabilizers in water under ambient conditions and furnishes the allyl–aryl coupling products in high isolated yields with high stereospecificities as well as excellent chemo‐, regio‐ and E / Z ‐selectivities. The in situ generated PdNPs showed extraordinary catalytic activity (S/C up to 5000) even for the allyl–aryl coupling reactions of easily eliminated allylic carbonates under aqueous ambient conditions. The mechanism of the process has also been investigated.