4.7 Article

Copper(I) Iodide/Boron Trifluoride Etherate-Cocatalyzed Aerobic Dehydrogenative Reactions Applied in the Synthesis of Substituted Heteroaromatic Imidazo[1,2-a]pyridines

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 355, Issue 13, Pages 2686-2692

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201300333

Keywords

C(sp(3))H functionalization; copper; dehydrogenative coupling; imidazo[1, 2-a]pyridines; oxygen

Funding

  1. Natural Science Foundation of China [21042007, 21172162]
  2. Young National Natural Science Foundation of China [21202111]
  3. Young Natural Science Foundation of Jiangsu Province [BK2012174]
  4. PAPD
  5. Soochow University

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Compared with the well-known palladium-catalyzed oxidative dehydrogenation coupling reactions, similar transforms initiated by copper/oxygen have attracted more and more attention. We have investigated a novel construction of heteroaromatic imidazo[1,2-a]pyridines through copper(I) iodide/boron trifluoride etherate/oxygen-mediated dehydrogenative reactions of aryl alkyl or alkyl alkyl ketones with 2-aminopyridines. Four hydrogen atoms are removed and two new CN bonds are formed in one step via the imine formation and oxidative C(sp(3))H functionalization.

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