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Direct intermolecular aniline ortho-arylation via benzyne intermediates.

ABSTRACT: A method for direct, transition-metal-free ortho-arylation of anilines by aryl chlorides, bromides, fluorides, and triflates has been developed. This methodology provides the most direct approach to 2-arylanilines since no protecting or directing groups on nitrogen are required. The arylation is functional-group tolerant, with alkene, ether, trifluoromethyl, dimethylamino, carbonyl, chloro, and cyano functionalities tolerated. Phenylation of enantiopure binaphthyldiamine affords a product with >99% ee.

SUBMITTER: Truong T

PROVIDER: S-EPMC3518720 | biostudies-literature | 2012 Dec

REPOSITORIES: biostudies-literature

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Direct intermolecular aniline ortho-arylation via benzyne intermediates.

Truong Thanh T Daugulis Olafs O

Organic letters 20121113 23

A method for direct, transition-metal-free ortho-arylation of anilines by aryl chlorides, bromides, fluorides, and triflates has been developed. This methodology provides the most direct approach to 2-arylanilines since no protecting or directing groups on nitrogen are required. The arylation is functional-group tolerant, with alkene, ether, trifluoromethyl, dimethylamino, carbonyl, chloro, and cyano functionalities tolerated. Phenylation of enantiopure binaphthyldiamine affords a product with > ...[more]

PMID: 23148679

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