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Synthesis of Spiro-dihydroquinoline and Octahydrophenanthrene Derivatives via Palladium-Catalyzed Intramolecular Oxidative Arylation

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journal contribution
posted on 07.03.2017 by Zhong-Lin Zang, Shuklachary Karnakanti, Sheng Zhao, Ping Hu, Zhen Wang, Pan-Lin Shao, Yun He
A method for intramolecular sp2 C–H oxidative arylation of unactivated cyclic olefins has been developed to access spiro-dihydroquinoline and octahydrophenanthrene derivatives in a straightforward and efficient manner. Bearing picolinamide as a directing group, the alkenyl anilines cyclized to afford spiro-dihydroquinolines in moderate to excellent yields via direct oxidative arylation, while the alkenyl benzylamines furnished the octahydrophenanthrene derivatives in moderate yields via sequential oxidative arylation and double acetoxylation.

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