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Cobalt-catalyzed, aminoquinoline-directed coupling of sp(2) C-H bonds with alkenes.

ABSTRACT: 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.

SUBMITTER: Grigorjeva L

PROVIDER: S-EPMC4155791 | biostudies-literature | 2014 Sep

REPOSITORIES: biostudies-literature

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Cobalt-catalyzed, aminoquinoline-directed coupling of sp(2) C-H bonds with alkenes.

Grigorjeva Liene L Daugulis Olafs O

Organic letters 20140822 17

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, e ...[more]

PMID: 25146300

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