Activation of C–H Bonds via the Merger of Photoredox and Organocatalysis: A Coupling of Benzylic Ethers with Schiff Bases

[Image: see text] The photoredox-mediated coupling of benzylic ethers with Schiff bases has been accomplished. Direct benzylic C–H activation by a combination of a thiol catalyst with an iridium photocatalyst and subsequent radical–radical coupling with secondary aldimines affords a variety of β-ami...

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Autores principales: Hager, Dominik, MacMillan, David W. C.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4277755/
https://www.ncbi.nlm.nih.gov/pubmed/25457231
http://dx.doi.org/10.1021/ja5102695
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author Hager, Dominik
MacMillan, David W. C.
author_facet Hager, Dominik
MacMillan, David W. C.
author_sort Hager, Dominik
collection PubMed
description [Image: see text] The photoredox-mediated coupling of benzylic ethers with Schiff bases has been accomplished. Direct benzylic C–H activation by a combination of a thiol catalyst with an iridium photocatalyst and subsequent radical–radical coupling with secondary aldimines affords a variety of β-amino ether products in good to excellent yields. Mechanistic studies suggest that a reductive quenching pathway of the photocatalyst is operable.
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spelling pubmed-42777552015-11-17 Activation of C–H Bonds via the Merger of Photoredox and Organocatalysis: A Coupling of Benzylic Ethers with Schiff Bases Hager, Dominik MacMillan, David W. C. J Am Chem Soc [Image: see text] The photoredox-mediated coupling of benzylic ethers with Schiff bases has been accomplished. Direct benzylic C–H activation by a combination of a thiol catalyst with an iridium photocatalyst and subsequent radical–radical coupling with secondary aldimines affords a variety of β-amino ether products in good to excellent yields. Mechanistic studies suggest that a reductive quenching pathway of the photocatalyst is operable. American Chemical Society 2014-11-17 2014-12-10 /pmc/articles/PMC4277755/ /pubmed/25457231 http://dx.doi.org/10.1021/ja5102695 Text en Copyright © 2014 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Hager, Dominik
MacMillan, David W. C.
Activation of C–H Bonds via the Merger of Photoredox and Organocatalysis: A Coupling of Benzylic Ethers with Schiff Bases
title Activation of C–H Bonds via the Merger of Photoredox and Organocatalysis: A Coupling of Benzylic Ethers with Schiff Bases
title_full Activation of C–H Bonds via the Merger of Photoredox and Organocatalysis: A Coupling of Benzylic Ethers with Schiff Bases
title_fullStr Activation of C–H Bonds via the Merger of Photoredox and Organocatalysis: A Coupling of Benzylic Ethers with Schiff Bases
title_full_unstemmed Activation of C–H Bonds via the Merger of Photoredox and Organocatalysis: A Coupling of Benzylic Ethers with Schiff Bases
title_short Activation of C–H Bonds via the Merger of Photoredox and Organocatalysis: A Coupling of Benzylic Ethers with Schiff Bases
title_sort activation of c–h bonds via the merger of photoredox and organocatalysis: a coupling of benzylic ethers with schiff bases
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4277755/
https://www.ncbi.nlm.nih.gov/pubmed/25457231
http://dx.doi.org/10.1021/ja5102695
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