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Pure Appl. Chem. Vol. 74, No. 1, pp. 181-186 (2002)

Pure and Applied Chemistry

Vol. 74, Issue 1

Addition reactions of heteroatom-COX (X = OR, NR2, COOR) species with alkynes*

Masato Tanaka1,2, and Ruimao Hua2

1Tokyo Institute of Technology, Chemical Resources Laboratory, 4259 Nagatsuda, Midori-ku, Yokohama 226-8503, Japan; 2National Institute of Advanced Industrial Science and Technology, Tsukuba Central 5, Tsukuba, Ibaraki 305-8565, Japan

Abstract: Heteroatom-COX species where the heteroatom is Cl, S, or Sn and X is alkoxy, amino, or alkoxycarbonyl group were found to add to the triple bond of alkynes regio- and stereoselectively in the presence of Rh, Pd, or Ni catalyst. Scope and limitation of these synthetic reactions were disclosed. Mechanistic study revealed that oxidative addition of these heteroatom-COX bonds readily took place and the resulting adducts were isolable and characterized by X-ray diffraction analysis. Synthetic applications of the catalytic reactions were also demonstrated.

*Lecture presented at the 11th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-11), Taipei, Taiwan, 22-26 July 2001. Other presentations are presented in this issue, pp.1-186.
**Corresponding author.


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