Journal
CHEMICAL SCIENCE
Volume 3, Issue 3, Pages 883-886Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c1sc00661d
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Funding
- National Basic Research Program of China [2010CB833201, 2010CB923303]
- China Postdoctoral Science Foundation [20110490246]
- Peking University Shenzhen Graduate School
- National Natural Science Foundation of China [20902045, 91013009]
- Shenzhen Government [JC201005260103A]
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We describe a general dehydrogenation procedure to form alpha,beta-unsaturated aldehydes, ketones, esters and azobenzenes under very mild conditions, requiring catalytic commercial Pd(OAc)(2), a catalytic weak inorganic base and air as the sole oxidant. In the presence of a diazafluorenone ligand, this process converts aliphatic aldehydes to alpha,beta-unsaturated aldehydes in an open-flask fashion at ambient pressure and temperature. A broad spectrum of substrates, including aldehydes, ketones, esters, alcohols and hydrazines, were conveniently dehydrogenated under a relatively uniformed protocol. A mechanism involving beta-elimination-driven enolization equilibrium shift was proposed.
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