期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 54, 期 29, 页码 8458-8461出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201503620
关键词
aldehydes; homogeneous catalysis; iridium; retro-hydroformylation; synthesis gas
资金
- Ministry of Education, Culture, Sports, Science and Technology (MEXT
- Japan)
- Takasago International Corporation Award in Organic Synthetic Chemistry (Japan)
- Sasakawa Scientific Research Grant from The Japan Science Society
Hydroformylation, a reaction that adds carbon monoxide and dihydrogen across an unsaturated carbon-carbon multiple bond, has been widely employed in the chemical industry since its discovery in 1938. In contrast, the reverse reaction, retro-hydroformylation, has seldom been studied. The retro-hydroformylation reaction of an aldehyde into an alkene and synthesis gas (a mixture of carbon monoxide and dihydrogen) in the presence of a cyclopentadienyl iridium catalyst is now reported. Aliphatic aldehydes were converted into the corresponding alkenes in up to 91% yield with concomitant release of carbon monoxide and dihydrogen. Mechanistic control experiments indicated that the reaction proceeds by retro-hydroformylation and not by a sequential decarbonylation-dehydrogenation or dehydrogenation-decarbonylation process.
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