Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 48, Pages 17151-17155Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201604503
Keywords
diboronic acid; hydrogen atom transfer; metal-free; nitrogen heterocycles; water
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Funding
- National Natural Science Foundation of China (NSFC) [21372118]
- Fundamental Research Funds for the Central Universities [KYTZ201604]
- Foundation Research Project of Jiangsu Province (The Natural Science Foundation) [BK20141359]
- 333 High Level Talent Project of JiangSu Province
- Grants-in-Aid for Scientific Research [26620040] Funding Source: KAKEN
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A hydrogenation of N-heterocycles mediated by diboronic acid with water as the hydrogen atom source is reported. A variety of N-heterocycles can be hydrogenated with medium to excellent yields within 10min. Complete deuterium incorporation from stoichiometric D2O onto substrates further exemplifies the H/D atom sources. Mechanism studies reveal that the reduction proceeds with initial 1,2-addition, in which diboronic acid synergistically activates substrates and water via a six-membered ring transition state.
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