Download PDF
Synthesis 1996; 1996(1): 1-24
DOI: 10.1055/s-1996-4175
review
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

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