Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2011, Issue 20-21, Pages 3748-3754Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201100280
Keywords
Cumulenes; Allenes; Alkynes; Platinum; Hydrogenation; Reductive cyclization; Density functional calculations
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Funding
- Korean Government, National Research Foundation of Korea [2010-0029617, 2010-0016079, 2010-0002396]
- National Research Foundation of Korea [2010-0002396] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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Upon platinum-catalyzed hydrogenation, allenynes underwent reductive cyclization to provide hetero- and carbo-cycles with completely controlled regio- and stereoselectivity. By employing hydrogen as a reductant, the use of stoichiometric amounts of toxic organometallic reductants was avoided, leading to clean and cost-effective synthesis. A possible catalytic cycle is proposed on the basis of a deuterium-labeling study and theoretical calculations.
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