Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 18, Pages 6718-6722Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201500629
Keywords
1,5-H radical shift; alkenes; C-H functionalization; cross-coupling; trifluoromethylation
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Funding
- National Natural Science Foundation of China [21302088, 21302087]
- National Basic Research Program of China [2013CB834802]
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By involving the reversal of conventional reactivity expectations without external oxidants, we describe a novel and convenient protocol of remote cross-coupling of carbonyl compounds with a series of common and simple nucleophiles. This cross-coupling is triggered by radical trifluoromethylation of alkenes, thereby achieving highly selective remote difunctionalization of alkenes and alpha-position of the carbonyl group for facile access to trifluoromethyl alpha-halo- and alpha-cyanocarbonyl compounds. The reaction exhibits a broad substrate scope with excellent functionality tolerance and many different types of nucleophiles; further synthetic applicability of the obtained compounds proved to be suitable, thus showing great potential for synthetic utility.
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