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Brønsted acid cocatalysis in copper(I)-photocatalyzed α-amino C−H bond functionalization

Citation

Nicholls, TP and Constable, GE and Robertson, JC and Gardiner, MG and Bissember, AC, Brønsted acid cocatalysis in copper(I)-photocatalyzed α-amino C−H bond functionalization, ACS Catalysis, 6, (1) pp. 451-457. ISSN 2155-5435 (2016) [Refereed Article]

Copyright Statement

2015 American Chemical Society

DOI: doi:10.1021/acscatal.5b02014

Abstract

We have exploited a bis(1,10-phenanthroline)copper(I) visible light photocatalyst (VLP), [Cu(dap)2]+, to effect the direct α-CH functionalization of amines. To our knowledge, this represents the first example of the oxidation of amines that are ultimately incorporated into synthetic targets by a copper(I) VLP. We have utilized this approach to rapidly prepare unprecedented octahydroisoquinolino[2,1-a]pyrrolo[3,4-c]quinoline frameworks and exploited this process to synthesize a novel aglycone analogue of the natural product incargranine B. Most significantly, our studies suggest that the presence of trifluoroacetic acid (TFA) is crucial in mediating the aerobic oxidative quenching of a putative photoexcited copper(I) species involved in the catalytic cycle.

Item Details

Item Type:Refereed Article
Keywords:photocatalysis, [Cu(dap)2]Cl, trifluoroacetic acid, aerobic oxidation, visible light
Research Division:Chemical Sciences
Research Group:Organic Chemistry
Research Field:Organic Chemical Synthesis
Objective Division:Expanding Knowledge
Objective Group:Expanding Knowledge
Objective Field:Expanding Knowledge in the Chemical Sciences
Author:Nicholls, TP (Mr Thomas Nicholls)
Author:Constable, GE (Miss Grace Constable)
Author:Robertson, JC (Mr Johnathon Robertson)
Author:Gardiner, MG (Associate Professor Michael Gardiner)
Author:Bissember, AC (Dr Alex Bissember)
ID Code:105579
Year Published:2016
Web of Science® Times Cited:17
Deposited By:Chemistry
Deposited On:2016-01-08
Last Modified:2017-08-21
Downloads:0

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