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Multifunctional Palladium Catalysis. 2. Tandem Haloallylation Followed by Wacker-Tsuji Oxidation or Sonogashira Cross-Coupling

Avinash N. Thadani and Viresh H. Rawal*

*Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, Email:

A. N. Thadani, V. H. Rawal, Org. Lett., 2002, 4, 4321-4323.

DOI: 10.1021/ol0269603

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Multifunctional palladium catalysis allows a one-pot stereocontrolled synthesis of tetrasubstituted methyl ketones and enynes. The homogeneous palladium dihalide catalyst is used for the bromo-/chloroallylation of alkynes and in situ for subsequent Wacker-Tsuji oxidation or Sonogashira cross-coupling.

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reaction pathway

Key Words

Wacker-Tsuji Oxidation, Sonogashira Coupling, Haloallylation, Carbonyl Compounds, Enynes, Oxygen

ID: J54-Y2002-770