Issue 10, 2017

Merging photoredox catalysis with transition metal catalysis: site-selective C4 or C5-H phosphonation of 8-aminoquinoline amides

Abstract

A simple and efficient protocol for the transition metal-catalyzed site-selective C–H phosphonation of 8-aminoquinolines with diarylphosphine oxide or H-phosphonate diesters was developed via a photoredox process. This reaction features high regioselectivity at the C4 or C5 position under mild and simple conditions (with a catalytic amount of silver salt at room temperature). Note that the C4 position of 8-aminoquinoline is an unusual reactive site.

Graphical abstract: Merging photoredox catalysis with transition metal catalysis: site-selective C4 or C5-H phosphonation of 8-aminoquinoline amides

Supplementary files

Article information

Article type
Research Article
Submitted
19 apr 2017
Accepted
27 jun 2017
First published
28 jun 2017

Org. Chem. Front., 2017,4, 1981-1986

Merging photoredox catalysis with transition metal catalysis: site-selective C4 or C5-H phosphonation of 8-aminoquinoline amides

H. Qiao, S. Sun, Y. Zhang, H. Zhu, X. Yu, F. Yang, Y. Wu, Z. Li and Y. Wu, Org. Chem. Front., 2017, 4, 1981 DOI: 10.1039/C7QO00305F

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