Carbene-catalyzed reductive coupling of nitrobenzyl bromide and nitroalkene via the single-electron-transfer (SET) process and formal 1,4-addition

A carbene-catalyzed reductive 1,4-addition of nitrobenzyl bromides to nitroalkenes is disclosed. The reaction proceeds via a carbene-enabled single-electron-transfer process that generates radicals as key intermediates. The present study expands the potentials of carbene catalysis and offers unusual...

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Main Authors:	Wang, Yuhuang, Du, Yu, Huang, Xuan, Wu, Xingxing, Zhang, Yuexia, Yang, Song, Chi, Robin Yonggui
Other Authors:	School of Physical and Mathematical Sciences
Format:	Article
Language:	English
Published:	2017
Subjects:	Science::Chemistry Single-Electron-Transfer Nitrobenzyl Bromide
Online Access:	https://hdl.handle.net/10356/85595 http://hdl.handle.net/10220/43776
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Institution:	Nanyang Technological University
Language:	English

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spelling	sg-ntu-dr.10356-855952023-02-28T19:54:36Z Carbene-catalyzed reductive coupling of nitrobenzyl bromide and nitroalkene via the single-electron-transfer (SET) process and formal 1,4-addition Wang, Yuhuang Du, Yu Huang, Xuan Wu, Xingxing Zhang, Yuexia Yang, Song Chi, Robin Yonggui School of Physical and Mathematical Sciences Science::Chemistry Single-Electron-Transfer Nitrobenzyl Bromide A carbene-catalyzed reductive 1,4-addition of nitrobenzyl bromides to nitroalkenes is disclosed. The reaction proceeds via a carbene-enabled single-electron-transfer process that generates radicals as key intermediates. The present study expands the potentials of carbene catalysis and offers unusual transformations for common substrates in organic synthesis. Ministry of Education (MOE) Nanyang Technological University National Research Foundation (NRF) Accepted version We acknowledge financial support by the Singapore National Research Foundation (NRF-NRFI2016-06), the Ministry of Education of Singapore (MOE2013-T2-2-003), Nanyang Technological University (NTU, Singapore), China’s Ministry of Education, National Key program for Basic Research (No. 2010CB 126105), Thousand Talent Plan (700059143302), and National Natural Science Foundation of China (No. 21132003; No. 21472028) and support by the Guizhou Province Returned Oversea Student Science and Technology Activity Program, Science and Technology of Guizhou Province, and Guizhou University. 2017-09-20T09:06:20Z 2019-12-06T16:06:48Z 2017-09-20T09:06:20Z 2019-12-06T16:06:48Z 2017 Journal Article Wang, Y., Du, Y., Huang, X., Wu, X., Zhang, Y., Yang, S. & Chi, R. Y. (2017). Carbene-catalyzed reductive coupling of nitrobenzyl bromide and nitroalkene via the single-electron-transfer (SET) process and formal 1,4-addition. Organic Letters, 19(3), 632-635. https://dx.doi.org/10.1021/acs.orglett.6b03792 1523-7060 https://hdl.handle.net/10356/85595 http://hdl.handle.net/10220/43776 10.1021/acs.orglett.6b03792 3 19 632 635 en NRF-NRFI2016-06 MOE2013-T2-2-003 Organic Letters This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.6b03792. 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 Single-Electron-Transfer Nitrobenzyl Bromide
spellingShingle	Science::Chemistry Single-Electron-Transfer Nitrobenzyl Bromide Wang, Yuhuang Du, Yu Huang, Xuan Wu, Xingxing Zhang, Yuexia Yang, Song Chi, Robin Yonggui Carbene-catalyzed reductive coupling of nitrobenzyl bromide and nitroalkene via the single-electron-transfer (SET) process and formal 1,4-addition
description	A carbene-catalyzed reductive 1,4-addition of nitrobenzyl bromides to nitroalkenes is disclosed. The reaction proceeds via a carbene-enabled single-electron-transfer process that generates radicals as key intermediates. The present study expands the potentials of carbene catalysis and offers unusual transformations for common substrates in organic synthesis.
author2	School of Physical and Mathematical Sciences
author_facet	School of Physical and Mathematical Sciences Wang, Yuhuang Du, Yu Huang, Xuan Wu, Xingxing Zhang, Yuexia Yang, Song Chi, Robin Yonggui
format	Article
author	Wang, Yuhuang Du, Yu Huang, Xuan Wu, Xingxing Zhang, Yuexia Yang, Song Chi, Robin Yonggui
author_sort	Wang, Yuhuang
title	Carbene-catalyzed reductive coupling of nitrobenzyl bromide and nitroalkene via the single-electron-transfer (SET) process and formal 1,4-addition
title_short	Carbene-catalyzed reductive coupling of nitrobenzyl bromide and nitroalkene via the single-electron-transfer (SET) process and formal 1,4-addition
title_full	Carbene-catalyzed reductive coupling of nitrobenzyl bromide and nitroalkene via the single-electron-transfer (SET) process and formal 1,4-addition
title_fullStr	Carbene-catalyzed reductive coupling of nitrobenzyl bromide and nitroalkene via the single-electron-transfer (SET) process and formal 1,4-addition
title_full_unstemmed	Carbene-catalyzed reductive coupling of nitrobenzyl bromide and nitroalkene via the single-electron-transfer (SET) process and formal 1,4-addition
title_sort	carbene-catalyzed reductive coupling of nitrobenzyl bromide and nitroalkene via the single-electron-transfer (set) process and formal 1,4-addition
publishDate	2017
url	https://hdl.handle.net/10356/85595 http://hdl.handle.net/10220/43776
_version_	1759856871915651072

Carbene-catalyzed reductive coupling of nitrobenzyl bromide and nitroalkene via the single-electron-transfer (SET) process and formal 1,4-addition

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