Heterocycles via Cross Dehydrogenative Coupling by Ananya Srivastava & Chandan K. Jana

Author:Ananya Srivastava & Chandan K. Jana
Language: eng
Format: epub
ISBN: 9789811391446
Publisher: Springer Singapore

Using copper(I) 4,6-dimethylpyrimidine-2-thiolate cluster as a catalyst, Li and Lang group developed an efficient and convenient method for acceptorless dehydrogenative coupling of alcohols to produce exclusively the ketone derivatives in good-to-excellent yields (Scheme 25) [40]. The substrate scope was shown on a wide variety of secondary and primary alcohols, notably ferrocenylmethanol nicely underwent cross-coupling with benzyl alcohol to give the corresponding alkylated product in 96% yield under the optimized reaction conditions. It should be pointed out that they carried out a reaction in gram scale (10 mmol) and obtained the desired alkylated ketone product in 72% yield using standard reaction conditions. Substrate scope has been extended to γ-amino and 2-aminobenzyl alcohols to get pyridines and quinolines, respectively, through cross-coupling annulation process in one pot. It was also observed that SH group of ligand 4,6-dimethylpyrimidine-2-thiolate plays a key role in controlling activity and selectivity of the present transformation through metal–ligand cooperation.

Scheme 25The Cu-catalyzed system by Li and Lang

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