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Synthesis 1996; 1996(8): 949-953
DOI: 10.1055/s-1996-4323
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Synthesis of Phenolic Biaryls and p-Terphenyls and Their Heteroaromatic Analogs via a Cycloaddition Route Using 4-Aryl-2-silyloxybuta-1,3-dienes and Electron-Deficient Alkynes

Yoshihiko Yamamoto, Keiko Nunokawa, Masatomi Ohno, Shoji Eguchi*
  • *Institute of Applied Organic Chemistry, Faculty of Engineering, Nagoya University, Chikusa, Nagoya 464-01, Japan, Fax +81(52)7893199
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Publication Date:
31 December 2000 (online)

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A one-pot synthesis of phenolic biaryls and p-terphenyls by a [4+2] cycloaddition of 4-aryl-2-silyloxybuta-1,3-dienes with electron-deficient alkynes followed by oxidative aromatization of the resulting cycloadducts is reported.

4-aryl-2-silyloxybuta-1,3-diene - electron-deficient alkyne - Diels-Alder reaction - oxidative aromatization - biphenyl