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Copper-catalyzed tandem phosphorylative allenylation/cyclization of 1-(o-aminophenyl)prop-2-ynols with the P(O)–H species: access to C2-phosphorylmethylindoles

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Abstract

A novel cascade reaction of 1-(o-aminophenyl)prop-2-ynols with the P(O)–H species has been developed, which leads to C2-phosphorylmethylindoles with sequential C–P and C–N bond formation in a single operation. Mechanistic studies suggest that the reaction proceeds via a carbocation initiated tandem phosphorylation/5-exo-dig cyclization, which firstly demonstrates the tandem allene formation/cyclization as a new reaction mode of 1-(o-aminophenyl)prop-2-ynols.

Graphical abstract: Copper-catalyzed tandem phosphorylative allenylation/cyclization of 1-(o-aminophenyl)prop-2-ynols with the P(O)–H species: access to C2-phosphorylmethylindoles

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Article information


Submitted
05 Feb 2020
Accepted
06 Mar 2020
First published
10 Mar 2020

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

Copper-catalyzed tandem phosphorylative allenylation/cyclization of 1-(o-aminophenyl)prop-2-ynols with the P(O)–H species: access to C2-phosphorylmethylindoles

X. Liu, Y. Zou, H. Ni, J. Zhang, H. Dong and L. Chen, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/D0QO00159G

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