Tuning Chemoselectivity in Iron‐Catalyzed Sonogashira‐Type Reactions Using a Bisphosphine Ligand with Peripheral Steric Bulk: Selective Alkynylation of Nonactivated Alkyl Halides | Zendy

Hatakeyama Takuji | Zendy; Okada Yoshihiro | Zendy; Yoshimoto Yuya | Zendy; Nakamura Masaharu | Zendy

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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.

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