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Oxygen switch in visible-light photoredox catalysis: Radical additions and cyclizations and unexpected C-C-bond cleavage reactions

Zhu, S and Das, A and Bui, L and Zhou, H and Curran, DP and Rueping, M (2013) Oxygen switch in visible-light photoredox catalysis: Radical additions and cyclizations and unexpected C-C-bond cleavage reactions. Journal of the American Chemical Society, 135 (5). 1823 - 1829. ISSN 0002-7863

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Abstract

Visible light photoredox catalyzed inter- and intramolecular C-H functionalization reactions of tertiary amines have been developed. Oxygen was found to act as chemical switch to trigger two different reaction pathways and to obtain two different types of products from the same starting material. In the absence of oxygen, the intermolecular addition of N,N-dimethyl-anilines to electron-deficient alkenes provided γ-amino nitriles in good to high yields. In the presence of oxygen, a radical addition/cyclization reaction occurred which resulted in the formation of tetrahydroquinoline derivatives in good yields under mild reaction conditions. The intramolecular version of the radical addition led to the unexpected formation of indole-3-carboxaldehyde derivatives. Mechanistic investigations of this reaction cascade uncovered a new photoredox catalyzed C-C bond cleavage reaction. © 2013 American Chemical Society.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Zhu, S
Das, A
Bui, L
Zhou, H
Curran, DPcurran@pitt.eduCURRAN
Rueping, M
Date: 6 February 2013
Date Type: Publication
Journal or Publication Title: Journal of the American Chemical Society
Volume: 135
Number: 5
Page Range: 1823 - 1829
DOI or Unique Handle: 10.1021/ja309580a
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0002-7863
MeSH Headings: Amines--chemical synthesis; Amines--chemistry; Catalysis; Cyclization; Free Radicals--chemistry; Light; Molecular Structure; Oxidation-Reduction; Oxygen--chemistry; Photochemical Processes
PubMed ID: 23330701
Date Deposited: 18 Jul 2014 21:17
Last Modified: 02 Feb 2019 15:58
URI: http://d-scholarship.pitt.edu/id/eprint/22248

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