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Aromatic‐Amide‐Derived Olefins as a Springboard: Isomerization‐Initiated Palladium‐Catalyzed Hydrogenation of Olefins and Reductive Decarbonylation of Acyl Chlorides with Hydrosilane
Author(s) -
Bai XingFeng,
Xu LiWen,
Zheng LongSheng,
Jiang JianXiong,
Lai GuoQiao,
Shang JunYan
Publication year - 2012
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.201200039
Subject(s) - decarbonylation , isomerization , chemistry , amide , moiety , palladium , olefin fiber , catalysis , ligand (biochemistry) , medicinal chemistry , double bond , organic chemistry , biochemistry , receptor
A highly efficient catalytic protocol for the isomerization of substituted amide‐derived olefins is presented that successfully uses a hydride palladium catalyst system generated from [PdCl 2 (PPh 3 ) 2 ] and HSi(OEt) 3 . The Z to E isomerization was carried out smoothly and resulted in geometrically pure substituted olefins. Apart from the cis – trans isomerization of double bonds, the selective reduction of terminal olefins and activated alkenes was performed with excellent functional group tolerance in the presence of an amide‐derived olefin ligand, and the products were obtained in high isolated yields (up to >99 %). Furthermore, the palladium/hydrosilane system was able to promote the reductive decarbonylation of benzoyl chloride when a ( Z )‐olefin with an aromatic amide moiety was used as a ligand.