Synfacts 2006(8): 0781-0781  
DOI: 10.1055/s-2006-941960
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

A Quick Approach to Valuable Building Blocks Using Multiple Benzidine Rearrangements

Contributor(s): Timothy M. Swager, Jean Bouffard
H.-M. Kang, Y.-K. Lim, I.-J. Shin, H.-Y. Kim, C.-G. Cho*
Hanyang University, Seoul, Korea
Further Information

Publication History

Publication Date:
21 July 2006 (online)

Significance

Cho and co-workers report a clever strategy, founded on a modern re-exploration of the benzidine rearrangement chemistry, which enables the very rapid preparation of a great diversity of building blocks containing the benzidine (4,4′-diaminobiphenyl) unit. Palladium-catalyzed C-N bond formation between ortho- or meta-substituted N-aryl hydrazines and halobenzenes gives N,N′-diaryl hydrazines in excellent yield. Treatment with hydrochloric acid affords the desired rearranged benzidines in a selective manner.