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DOI: 10.1055/s-2000-8239
Selective Synthesis of Tetraphenylenes and Biphenylenes Using Copper-Catalyzed Coupling of Zincacyclopentadienes
Publication History
Publication Date:
31 December 2000 (online)
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The intramolecular coupling of benzoannelated zincacyclopentadiene using CuCl2 produced 1,8-dibromobiphenylene selectively in a good yield. On the contrary, the intermolecular coupling of zincacyclopentadiene produced 2,3,6,7,10,11,14,15-octamethoxytetraphenylene selectively in a synthetically reasonable yield under different reaction conditions. The reactions of 2,2′-dilithio-4,4′,5,5′-tetramethoxybiphenyl and 2,2′-dilithio-4,4′,5,5′-tetrakis(tert-butyldimethylsilyloxy)biphenyl with CuCl2 in THF unexpectedly produced the corresponding tetraphenylene derivatives, instead of the desired biphenylene derivatives. Octamethoxytetraphenylene was used to synthesize octaacetoxytetraphenylene in a quantitative yield either directly or through octahydroxytetraphenylene.
arenes - copper - zinc - intramolecular coupling - intermolecular coupling