The Journal of Organic Chemistry

Synthetically useful aryl-aryl bond formation via Grignard generation and trapping of arynes. A one-step synthesis of p-terphenyl and unsymmetrical biaryls

H Hart, K Harada, CJF Du

Index: Hart, Harold; Harada, Katsumasa; Du, Chi-Jen Frank Journal of Organic Chemistry, 1985 , vol. 50, # 17 p. 3104 - 3110

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Citation Number: 82

Abstract

A one-pot route to p-terphenyls is described. Addition of 1, 4-dibromo-2, 5-diiodobenzene, 1, to excess aryl Grignard reagent gives the terphenyl di-Grignard 2 and the trihalo mono- Grignard 5. After aqueous quench, p-terphenyls are isolated in 30% to 50+% yield (Table I). This yield can be improved to 70-8070 by adding potassium tert-butoxide or lithium Btramethylpiperidide to the reaction mixture prior to workup. Mechanisms involving ...