Carbene-catalysed reductive coupling of nitrobenzyl bromides and activated ketones or imines via single-electron-transfer process

Bao-Sheng Li, Yuhuang Wang, Rupert S. J. Proctor, Yuexia Zhang, Richard D. Webster, Song Yang, Baoan Song and Yonggui Robin Chi ()
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Bao-Sheng Li: Nanyang Technological University, School of Physical & Mathematical Sciences
Yuhuang Wang: Nanyang Technological University, School of Physical & Mathematical Sciences
Rupert S. J. Proctor: Nanyang Technological University, School of Physical & Mathematical Sciences
Yuexia Zhang: Nanyang Technological University, School of Physical & Mathematical Sciences
Richard D. Webster: Nanyang Technological University, School of Physical & Mathematical Sciences
Song Yang: Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District
Baoan Song: Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District
Yonggui Robin Chi: Nanyang Technological University, School of Physical & Mathematical Sciences

Nature Communications, 2016, vol. 7, issue 1, 1-8

Abstract: Abstract Benzyl bromides and related molecules are among the most common substrates in organic synthesis. They are typically used as electrophiles in nucleophilic substitution reactions. These molecules can also be activated via single-electron-transfer (SET) process for radical reactions. Representative recent progress includes α-carbon benzylation of ketones and aldehydes via photoredox catalysis. Here we disclose the generation of (nitro)benzyl radicals via N-heterocyclic carbene (NHC) catalysis under reductive conditions. The radical intermediates generated via NHC catalysis undergo formal 1,2-addition with ketones to eventually afford tertiary alcohol products. The overall process constitutes a formal polarity-inversion of benzyl bromide, allowing a direct coupling of two initially electrophilic carbons. Our study provides a new carbene-catalysed reaction mode that should enable unconventional transformation of (nitro)benzyl bromides under mild organocatalytic conditions.

Date: 2016
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DOI: 10.1038/ncomms12933

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