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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Item Type: |
Article
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Status: |
Published |
Creators/Authors: |
Creators | Email | Pitt Username | ORCID ![](/images/orcid_id_24x24.png) |
---|
Zhu, S | | | | Das, A | | | | Bui, L | | | | Zhou, H | | | | Curran, DP | curran@pitt.edu | CURRAN | | Rueping, M | | | |
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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-dev.library.pitt.edu/id/eprint/22248 |
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