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Li, Minghong; Shang, Ming; Xu, Hui; Wang, Xing; Dai, Hui-Xiong; Yu, Jin-Quan (, Organic Letters)
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Kong, Wei-Jun; Shao, Qian; Li, Ming-Hong; Zhou, Zeng-Le; Xu, Hui; Dai, Hui-Xiong; Yu, Jin-Quan (, Organometallics)
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Lu, Ming-Zhu; Chen, Xing-Rong; Xu, Hui; Dai, Hui-Xiong; Yu, Jin-Quan (, Chemical Science)Although chelation-assisted C–H olefination has been intensely investigated, Pd( ii )-catalyzed C–H olefination reactions are largely restricted to acrylates and styrenes. Here we report a quinoline-derived ligand that enables the Pd( ii )-catalyzed olefination of the C(sp 2 )–H bond with simple aliphatic alkenes using a weakly coordinating monodentate amide auxiliary. Oxygen is used as the terminal oxidant with catalytic copper as the co-oxidant. A variety of functional groups in the aliphatic alkenes are tolerated. Upon hydrogenation, the ortho -alkylated product can be accessed. The utility of this reaction is also demonstrated by the late-stage diversification of drug molecules.more » « less
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