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Synthesis 1996; 1996(1): 1-24
DOI: 10.1055/s-1996-4175
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Palladium-Catalyzed Hydrogenolysis of Allylic and Propargylic Compounds with Various Hydrides

Jiro Tsuji* , Tadakatsu Mandai
  • *Department of Applied Chemistry, Okayama University of Science, Ridai-cho, Okayama 700, Japan, Fax +81(86)2526891
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Publikationsdatum:
31. Dezember 2000 (online)

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Palladium-catalyzed hydrogenolysis of allylic compounds with various hydride sources has two important synthetic applications. One application is the preparation of alkenes. Regioselective hydrogenolysis of terminal allylic compounds with triethylammonium formate to give 1-alkenes is particularly useful. A number of synthetic applications of regio- and stereoselective hydrogenolysis developed recently are surveyed. The second application is the use of the allyl group as a protecting group for carboxylic acids, alcohols, and amines. Deprotection by palladium-catalyzed hydrogenolysis proceeds under mild conditions. Allyl protection is attracting much attention as a useful method. Allenes or alkynes are obtained by the hydrogenolysis of propargylic compounds, the chemoselectivity depends on the structures of propargylic compounds.

formic acid - allyl as protecting group - 1-alkene formation - allene formation - internal alkyne formation

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