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Tuning Chemoselectivity in Iron‐Catalyzed Sonogashira‐Type Reactions Using a Bisphosphine Ligand with Peripheral Steric Bulk: Selective Alkynylation of Nonactivated Alkyl Halides
Author(s) -
Hatakeyama Takuji,
Okada Yoshihiro,
Yoshimoto Yuya,
Nakamura Masaharu
Publication year - 2011
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.201104125
Subject(s) - chemoselectivity , alkyl , alkynylation , steric effects , halide , chemistry , ligand (biochemistry) , phosphine , sonogashira coupling , combinatorial chemistry , catalysis , reagent , organic chemistry , medicinal chemistry , palladium , biochemistry , receptor
The incredible bulk : A highly C sp 3‐center‐selective alkynylation of nonactivated alkyl halides with the corresponding Grignard reagents is achieved by using the iron‐phosphine complex 1 . Primary and secondary alkyl iodides, bromides, and chlorides take part in the reaction to give the substituted alkynes in good to excellent yields. Sequential cyclization/cross‐coupling reactions are also demonstrated.