Substrate-Controlled Selectivity Switch in the Three-Component Coupling Involving Arynes, Aromatic Tertiary Amines, and CO2

Bhojgude, Sachin Suresh ; Roy, Tony ; Gonnade, Rajesh G. ; Biju, Akkattu T. (2016) Substrate-Controlled Selectivity Switch in the Three-Component Coupling Involving Arynes, Aromatic Tertiary Amines, and CO2 Organic Letters, 18 (20). pp. 5424-5427. ISSN 1523-7060

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Official URL: http://doi.org/10.1021/acs.orglett.6b02845

Related URL: http://dx.doi.org/10.1021/acs.orglett.6b02845

Abstract

The transition-metal-free multicomponent coupling involving arynes, aromatic tertiary amines, and CO2 is reported. The reaction exhibits switchable selectivity depending on the electronic nature of the aromatic amines used. With amines bearing electron-releasing/neutral groups as the nucleophilic trigger, the reaction afforded 2-arylamino benzoates via a nitrogen to oxygen alkyl group migration. Employing electron-deficient amines in the reaction furnished 2-aminoaryl benzoates proceeding via the aryl to aryl amino group migration resembling a Smiles rearrangement.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society
ID Code:128654
Deposited On:03 Nov 2022 06:50
Last Modified:03 Nov 2022 06:50

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