Work

Direct Intermolecular Aniline Ortho- Arylation via Benzyne Intermediates

Year: 2012

Type: article

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.

Source: Organic Letters

DOI: 10.1021/ol302875x

Authors: Thanh Truong, Olafs Daugulis

Institution: University of Houston

Language: English

Topic: Cyclization and Aryne Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Award: New Methods for Direct Carbon-Hydrogen Bond Functionalization