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Metal-Free Oxidation/C(sp3)[BOND]H Functionalization of Unactivated Alkynes Using Pyridine-N-Oxide as the External Oxidant

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  • We are grateful for financial support from the Chinese Academy of Sciences, MOST (973 project 2009CB82530), the Ministry of Education, and BASF (L.-Z.G.). We also thank the China Postdoctoral Science Foundation funded project (2011M501048), the Fundamental Research Funds for the Central Universities (WK2060190017), and the support of the K. C. Wang Education Foundation, Hong Kong.

Abstract

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Externally yours: 2,3-Dihydroquinolin-4(1H)-ones are obtained in moderate to good yields (40–84 %, see scheme) in a metal-free oxidation/C(sp3)[BOND]H functionalization of unactivated aryl alkynes. 2,6-Dichloropyridine-N-oxide is used as an external oxidant. In the reaction, a Brønsted acid, not a metal, plays a key role in the triple C[BOND]C bond activation.

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