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An Easy Route to N , N ‐Diarylhydrazines by Cu‐Catalyzed Arylation of Pyridine‐2‐carbaldehyde Hydrazones with Aryl Halides
Author(s) -
Wu Wei,
Li XinLe,
Fan XinHeng,
Yang LianMing
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201445
Subject(s) - chemistry , halide , aryl , pyridine , catalysis , medicinal chemistry , copper , combinatorial chemistry , aqueous solution , organic chemistry , alkyl
A copper‐catalyzed C–N coupling reaction is described for the preparation of pyridine‐2‐carbaldehyde N , N ‐diarylhydrazones by the arylation of N ‐mono‐ or ‐non‐substituted hydrazones with aryl bromides/iodides, and the subsequent conversion of the hydrazones into N , N ‐diarylhydrazines by a transimination process with an aqueous solution of H 2 NNH 2 . The reaction features the use of CuI as the catalyst without the need for external ligands. This methodology provides a convenient alternative to the synthesis of structurally diverse N , N ‐diarylhydrazines from simple, easily accessible precursors.