Vanadyl Acetylacetonate Catalyzed Methylenation of Imidazo[1,2-a]pyridines by Using Dimethylacetamide as a Methylene Source: Direct Access to Bis(imidazo[1,2-a]pyridin-3-yl)methanes

Authors

Pinku Kaswan, Birla Institute of Technology and Science, Pilani
Nitesh Kumar Nandwana, Birla Institute of Technology and Science, Pilani
Brenton DeBoef, University of Rhode IslandFollow
Anil Kumar, Birla Institute of Technology and Science, Pilani

Document Type

Article

Date of Original Version

6-30-2016

Abstract

An efficient protocol has been developed for the methylenation of imidazo[1,2-a]pyridines using dimethylacetamide (DMA) as methylene source in the presence of vanadyl acetylacetonate [VO(acac)2] as the catalyst and iodobenzene diacetate as the oxidant. The reaction involves coupling of sp3- and sp2-hybridized carbons and proceeds through the formation of an iminium ion. A wide variety of imidazo[1,2-a]pyridines were converted to bis(imidazo[1,2-a]pyridin-3-yl)methanes in good to excellent yields. A gram-scale reaction demonstrated the potential for the scale-up processes. (Figure presented.) .

Publication Title, e.g., Journal

Advanced Synthesis and Catalysis

Volume

358

Issue

13

Citation/Publisher Attribution

Kaswan, Pinku, Nitesh Kumar Nandwana, Brenton DeBoef, and Anil Kumar. "Vanadyl Acetylacetonate Catalyzed Methylenation of Imidazo[1,2-a]pyridines by Using Dimethylacetamide as a Methylene Source: Direct Access to Bis(imidazo[1,2-a]pyridin-3-yl)methanes." Advanced Synthesis and Catalysis 358, 13 (2016): 2108-2115. doi: 10.1002/adsc.201600225.