NHC And Visible Light-mediated Photoredox Co-catalyzed 1,4 ...

Jump to main content Jump to site search Issue 11, 2022

• Previous Article
• Next Article

From the journal:

Chemical Science

NHC and visible light-mediated photoredox co-catalyzed 1,4-sulfonylacylation of 1,3-enynes for tetrasubstituted allenyl ketones†

Lihong Wang,a Ruiyang Ma,a Jiaqiong Sun,b Guangfan Zheng *a and Qian Zhang *ac Author affiliations

* Corresponding authors

a Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of ChemistryNortheast Normal University, Changchun 130024, China E-mail: [email protected], [email protected]

b School of Environment, Northeast Normal University, Changchun 130117, China

c State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China

Abstract

The modulation of selectivity of highly reactive carbon radical cross-coupling for the construction of C–C bonds represents a challenging task in organic chemistry. N-Heterocyclic carbene (NHC) catalyzed radical transformations have opened a new avenue for acyl radical cross-coupling chemistry. With this method, highly selective cross-coupling of an acyl radical with an alkyl radical for efficient construction of C–C bonds was successfully realized. However, the cross-coupling reaction of acyl radicals with vinyl radicals has been much less investigated. We herein describe NHC and visible light-mediated photoredox co-catalyzed radical 1,4-sulfonylacylation of 1,3-enynes, providing structurally diversified valuable tetrasubstituted allenyl ketones. Mechanistic studies indicated that ketyl radicals are formed from aroyl fluorides via the oxidative quenching of the photocatalyst excited state, allenyl radicals are generated from chemo-specific sulfonyl radical addition to the 1,3-enynes, and finally, the key allenyl and ketyl radical cross-coupling provides tetrasubstituted allenyl ketones.

• This article is part of the themed collection: Most popular 2022 organic chemistry articles

This article is Open Access Please wait while we load your content... Something went wrong. Try again? About Cited by Related Download options Please wait...

Supplementary files

• Supplementary information PDF (15905K)
• Crystal structure data CIF (20K)

Article information

DOI https://doi.org/10.1039/D1SC06100C Article type Edge Article Submitted 04 Nov 2021 Accepted 06 Feb 2022 First published 10 Feb 2022 This article is Open Access All publication charges for this article have been paid for by the Royal Society of Chemistry

Download Citation

Chem. Sci., 2022,13, 3169-3175 BibTex EndNote MEDLINE ProCite ReferenceManager RefWorks RIS

Permissions

Request permissions

NHC and visible light-mediated photoredox co-catalyzed 1,4-sulfonylacylation of 1,3-enynes for tetrasubstituted allenyl ketones

L. Wang, R. Ma, J. Sun, G. Zheng and Q. Zhang, Chem. Sci., 2022, 13, 3169 DOI: 10.1039/D1SC06100C

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party commercial publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Tweet Share

Search articles by author

Lihong Wang Ruiyang Ma Jiaqiong Sun Guangfan Zheng Qian Zhang

Fetching data from CrossRef. This may take some time to load.

Loading related content

Spotlight

Advertisements

This website collects cookies to deliver a better user experience. See how this site uses Cookies. Do not sell my personal data. Este site coleta cookies para oferecer uma melhor experiência ao usuário. Veja como este site usa Cookies. Publishing

Journals

• Current Journals
• Archive Journals
• All Journals

Books

• Browse Books
• Series
• For Authors and Editors
• About

Databases

• Literature Updates
• ChemSpider
• The Merck Index*
• MarinLit

More

• For Members
• For Librarians
• Subscribe
• RSS Feeds
• Blogs
• Chemistry World
• Education in Chemistry
• Open Access
• Historical Collection