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Unexpected formation of porphyrinic enyne under Sonogashira conditions
Authors:Yi-Jen Chen  Shie-Ming Peng
Affiliation:a Department of Chemistry, National Chung Hsing University, 250 Kuo Kuang Road, Taichung 402, Taiwan
b Department of Chemistry, National Taiwan University, 1 Section 4 Roosevelt Road, Taipei 106, Taiwan
Abstract:Reaction of 5-iodo-10,15,20-tris(3,5-di-tert-butylphenyl)porphyrin with excess trimethylsilylacetylene under Sonogashira conditions gives an unexpected porphyrinic enyne suitable for further transformations. The NMR spectrum and structural analysis of the porphyrin enynes show that the substituent on the acetylene group is positioned above the porphyrin ring. This structural characteristic makes the microenvironment of the porphyrin center in a controllable fashion.
Keywords:Acetylenes   Cross-coupling   Enynes   Porphyrins
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