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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