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Paper | Special issue | Vol 90, No. 1, 2015, pp.252-260
Published online, 26th March, 2014
DOI: 10.3987/COM-14-S(K)15
Palladium-Catalyzed [3+2] Annulation of meso-Bromoporphyrin with Silylacetylenes and Desilylation of 8a-Silyl-7,8-dehydropurpurin

Norihito Fukui, Seiji Arai, Hiroshi Shinokubo, Hideki Yorimitsu,* and Atsuhiro Osuka*

*Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan


Palladium-catalyzed [3+2] annulation of meso-bromoporphyrins with trimethylsilyl-, tert-butyldimethylsilyl-, and triisopropylsilylacetylenes afforded 8a-silyl-7,8-dehydropurpurins. Protodesilylation of 8a-trimethylsilyl-7,8-de- hydropurpurin resulted in the first synthesis of an 8a,8b-unsubstituted 7,8-de hydropurpurin.