Journal
NATURE COMMUNICATIONS
Volume 7, Issue -, Pages -Publisher
NATURE PUBLISHING GROUP
DOI: 10.1038/ncomms12933
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Funding
- Singapore National Research Foundation (NRF)
- Ministry of Education
- Singapore Economic Development Board (EDB)
- GlaxoSmithKline (GSK)
- Nanyang Technological University (NTU)
- China's National Key program for Basic Research [2010CB 126105]
- Thousand Talent Plan, National Natural Science Foundation of China [21132003, 21472028]
- Returned Oversea Student Science and Technology Activity Program of Guizhou Province
- Guizhou Science and Technology Department's Key Program
- Guizhou University
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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 a-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.
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