Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 11, Pages 2942-2946Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201611692
Keywords
aldehydes; electron transfer; N-heterocyclic carbenes; organocatalysis; oxidation
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Funding
- National Natural Science Foundation of China [21132003, 21472028]
- Singapore National Research Foundation [NRF-NRFI2016-06]
- Ministry of Education of Singapore [MOE2013-T2-2-003]
- Nanyang Technological University (NTU, Singapore)
- China's Ministry of Education, Thousand Talent Plan
- Guizhou Province Returned Oversea Student Science and Technology Activity Program
- Science and Technology of Guizhou Province
- Guizhou University
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Simple and inexpensive polyhalides (CCl4 and C2Cl6) have been found to be effective and versatile oxidants in removing electrons from Breslow intermediates under N-heterocyclic carbene (NHC) catalysis. This oxidative reaction involves multiple single-electron-transfer (SET) processes and several radical intermediates. The alpha, beta, and gamma-carbon atoms of aldehydes and enals could be readily functionalized. Given the low cost of the oxidants and the broad applicability of the reactions, this study is expected to greatly enhance the feasibility of oxidative NHC catalysis for large-scale applications. Also this new SET radical process with polyhalides as single-electron oxidants will open a new avenue in the development of NHC-catalyzed radical reactions.
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