Cobalt-Catalyzed, Aminoquinoline-Directed Coupling of sp2 C–H Bonds with Alkenes | Zendy

Liene Grigorjeva | Zendy; Olafs Daugulis | Zendy

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Cobalt-Catalyzed, Aminoquinoline-Directed Coupling of sp² C–H Bonds with Alkenes

Author(s) -

Liene Grigorjeva,

Olafs Daugulis

Publication year - 2014

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol502005g

Subject(s) - chemistry , catalysis , nitro , cobalt , ether , solvent , alcohol , halogen , surface modification , benzoic acid , ethylene , functional group , medicinal chemistry , olefin fiber , oxygen , acrylic acid , organic chemistry , alkyl , polymer , monomer

A method for cobalt-catalyzed, aminoquinoline-directed ortho-functionalization of sp(2) C-H bonds with alkenes has been developed. Reactions proceed at room temperature in trifluoroethanol solvent, use oxygen from air as an oxidant, and require Mn(OAc)3 as a cocatalyst. Benzoic, heteroaromatic, and acrylic acid aminoquinoline amides react with ethylene as well as mono- and disubstituted alkenes affording products in good yields. Excellent functional group tolerance is observed; halogen, nitro, ether, and unprotected alcohol functionalities are compatible with the reaction conditions.

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