N-Heterocyclic carbene catalyzed radical coupling of aldehydes with redox-active esters

N-Heterocyclic carbene catalyzed radical coupling of aldehydes with redox-active esters

N-Heterocyclic carbene catalyzed radical reactions are challenging and underdeveloped. In a recent study, Ohmiya, Nagao and co-workers found that aldehyde carbonyl carbon centers can be coupled with alkyl radicals under NHC catalysis. An elegant aspect of this study is the use of a redox-active carb...

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Main Authors: Song, Runjiang, Chi, Robin Yonggui
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2020
Subjects:
Science::Chemistry::Organic chemistry
Ketones
N-Heterocyclic Carbenes
Online Access:https://hdl.handle.net/10356/137893
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-1378932023-02-28T19:47:29Z N-Heterocyclic carbene catalyzed radical coupling of aldehydes with redox-active esters Song, Runjiang Chi, Robin Yonggui School of Physical and Mathematical Sciences Science::Chemistry::Organic chemistry Ketones N-Heterocyclic Carbenes N-Heterocyclic carbene catalyzed radical reactions are challenging and underdeveloped. In a recent study, Ohmiya, Nagao and co-workers found that aldehyde carbonyl carbon centers can be coupled with alkyl radicals under NHC catalysis. An elegant aspect of this study is the use of a redox-active carboxylic ester that behaves as an single-electron oxidant to convert the Breslow intermediate into a radical adduct and concurrently release an alkyl radical intermediate as a reaction partner. NRF (Natl Research Foundation, S’pore) ASTAR (Agency for Sci., Tech. and Research, S’pore) MOE (Min. of Education, S’pore) Accepted version 2020-04-17T06:23:54Z 2020-04-17T06:23:54Z 2019 Journal Article Song, R., & Chi, R. Y. (2019). N-Heterocyclic carbene catalyzed radical coupling of aldehydes with redox-active esters. Angewandte Chemie International Edition, 58(26), 8628-8630. doi:10.1002/anie.201902792 1433-7851 https://hdl.handle.net/10356/137893 10.1002/anie.201902792 31124273 2-s2.0-85066272502 26 58 8628 8630 en Angewandte Chemie International Edition This is the peer reviewed version of the following article: Song, R., & Chi, Y. R. (2019). N-Heterocyclic carbene catalyzed radical coupling of aldehydes with redox-active esters. Angewandte Chemie International Edition, 58(26), 8628-8630, which has been published in final form at https://doi.org/10.1002/anie.201902792. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. application/pdf
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic Science::Chemistry::Organic chemistry
Ketones
N-Heterocyclic Carbenes
spellingShingle Science::Chemistry::Organic chemistry
Ketones
N-Heterocyclic Carbenes
Song, Runjiang
Chi, Robin Yonggui
N-Heterocyclic carbene catalyzed radical coupling of aldehydes with redox-active esters
description N-Heterocyclic carbene catalyzed radical reactions are challenging and underdeveloped. In a recent study, Ohmiya, Nagao and co-workers found that aldehyde carbonyl carbon centers can be coupled with alkyl radicals under NHC catalysis. An elegant aspect of this study is the use of a redox-active carboxylic ester that behaves as an single-electron oxidant to convert the Breslow intermediate into a radical adduct and concurrently release an alkyl radical intermediate as a reaction partner.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Song, Runjiang
Chi, Robin Yonggui
format Article
author Song, Runjiang
Chi, Robin Yonggui
author_sort Song, Runjiang
title N-Heterocyclic carbene catalyzed radical coupling of aldehydes with redox-active esters
title_short N-Heterocyclic carbene catalyzed radical coupling of aldehydes with redox-active esters
title_full N-Heterocyclic carbene catalyzed radical coupling of aldehydes with redox-active esters
title_fullStr N-Heterocyclic carbene catalyzed radical coupling of aldehydes with redox-active esters
title_full_unstemmed N-Heterocyclic carbene catalyzed radical coupling of aldehydes with redox-active esters
title_sort n-heterocyclic carbene catalyzed radical coupling of aldehydes with redox-active esters
publishDate 2020
url https://hdl.handle.net/10356/137893
_version_ 1759853518158561280

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