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Kusumoto S, Tatsuki T, Nozaki K. The Retro-Hydroformylation Reaction. Angew Chem Int Ed Engl. 2015;54(29):8458-61doi: 10.1002/anie.201503620.
Kusumoto, S., Tatsuki, T., & Nozaki, K. (2015). The Retro-Hydroformylation Reaction. Angewandte Chemie (International ed. in English), 54(29), 8458-61. https://doi.org/10.1002/anie.201503620
Kusumoto, Shuhei, et al. "The Retro-Hydroformylation Reaction." Angewandte Chemie (International ed. in English) vol. 54,29 (2015): 8458-61. doi: https://doi.org/10.1002/anie.201503620
Kusumoto S, Tatsuki T, Nozaki K. The Retro-Hydroformylation Reaction. Angew Chem Int Ed Engl. 2015 Jul 13;54(29):8458-61. doi: 10.1002/anie.201503620. Epub 2015 Jun 18. PMID: 26089259.
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Angew Chem Int Ed Engl. 2015 Jul 13;54(29):8458-61. doi: 10.1002/anie.201503620. Epub 2015 Jun 18.

The Retro-Hydroformylation Reaction.

Angewandte Chemie (International ed. in English)

Shuhei Kusumoto, Toshiumi Tatsuki, Kyoko Nozaki

Affiliations

  1. Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8656 (Japan).
  2. Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8656 (Japan). [email protected].

PMID: 26089259 DOI: 10.1002/anie.201503620

Abstract

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.

© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: aldehydes; homogeneous catalysis; iridium; retro-hydroformylation; synthesis gas

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