Arylamine synthesis

US6323366A · kind A · utility

Assignee

• Massachusetts Institute of Technology · US

Inventors

• John P. Wolfe · Watertown, US
• Jens Ahman · Sandwich, GB
• Joseph P. Sadighi · Boston, US
• Robert Singer · Burghausen, DE
• Stephen L. Buchwald · Newton, US

Key dates

• Filing date: Jul 24, 1998
• Grant date: Nov 27, 2001
• Expiry date: Jul 24, 2018

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C249/02
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The present invention provides a method for the preparation of a wide range of primary arylamines. The arylamines are prepared in two efficient, straightforward transformations: 1) an activated aryl group and an imine group are combined, in the presence of a transition metal catalyst, under conditions wherein the transition metal catalyst catalyzes the formation of a carbon-nitrogen bond between the activated carbon of the arene and the imine nitrogen; and 2) the resulting N-aryl imine is transformed, via any of a number of standard protocols, to the primary arylamine. The method of the invention may also be exploited in the preparation of vinylamines.