Synlett

Electroreductive Generation of Recyclable Organic Reductant from N, N′-Dioctyl-4, 4′-bipyridinium and Pd-Catalyzed Reductive Coupling of Aryl Halides

M Kuroboshi, R Kobayashi, T Nakagawa, H Tanaka

Index: Kuroboshi, Manabu; Kobayashi, Ryoto; Nakagawa, Takayuki; Tanaka, Hideo Synlett, 2009 , # 1 p. 85 - 88

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Citation Number: 3

Abstract

Abstract Electroreduction of N, N′-dioctyl-4, 4′-bipyridinium bis (triflimide)[C 8 V ²+][Tf 2 N- ] 2 in THF gave a dark blue solution of the corresponding quinoid C 8 V 0, which worked as an efficient organic reductant for Pd-catalyzed reductive coupling of aryl bromides to give the corresponding biphenyl derivatives in good yields. After usual workup,[C 8 V ²+][Tf 2 N-] 2 was recovered and reused for generation of the organic reductant C 8 V 0.