Quinoline as an Intramolecular Hydride Shuttle in the Deoxygenative Coupling Reaction of Alcohol and the Inert Methyl
Hui-Yun Wang1, Zhen-Yuan Liu1, Long-Xue Wang1
1College of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao 266109, China.
Abstract:
Reported herein is the C(sp3)-C(sp3) bond-forming at an unactivated C(sp3)-H bond via hydride transfer-initiated deoxygenative coupling reactions. Various polycyclic hydroquinolines were provided under metal-free conditions with excellent diastereoselectivity. Mechanistic study revealed that quinoline served as an intramolecular hydride shuttle to achieve the hydride abstraction and release in order. This methodology not only provides a practical strategy for direct deoxygenative coupling for the C(sp3)-C(sp3) bond-forming but also develops a new reaction type involving quinoline-enabled hydride transfer.
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