Migratory C(sp <sup>2</sup> )–H/C(sp <sup>3</sup> )–H Cross‐Coupling Enabled by Metallaphotoredox Catalysis
Abstract
Abstract Direct twofold C─H cross‐coupling between two readily available substrates offers a step‐ and atom‐economical alternative to traditional cross‐coupling reactions. Here we report the successful realization of this transformation through a dual catalytic platform that combines two orthogonal C─H activation modes: nickel‐catalyzed through‐space 1,4‐Ni/H shift and photoredox‐mediated hydrogen atom transfer (HAT). This synergistic strategy enables regio‐ and stereoselective synthesis of substituted alkenes or arenes from aryl bromides (or chlorides) and abundant alkanes with excellent chemo‐ and stereoselectivity. Mechanistic studies and DFT calculations indicate that HAT is the rate‐limiting step, while radical addition and subsequent reductive elimination collectively govern the observed regioselectivity.
Article Details
Authors (6)
Jingjie Yang
State Key Laboratory of Coordination Chemistry Jiangsu Key Laboratory of Advanced Organic Materials Chemistry and Biomedicine Innovation Center (ChemBIC) School of Chemistry and Chemical Engineering Nanjing University Nanjing 210093 China
Xinyu Li
Cell and Molecular Biology Program
Xinchen Wang
State Key Laboratory of Chemistry for NBC Hazards Protection, College of Chemistry
Jiabin Han
State Key Laboratory of Coordination Chemistry Jiangsu Key Laboratory of Advanced Organic Materials Chemistry and Biomedicine Innovation Center (ChemBIC) School of Chemistry and Chemical Engineering Nanjing University Nanjing 210093 China
You Wang
Shaolin Zhu
State Key Laboratory of Coordination Chemistry, Chemistry and Biomedicine Innovation Center (ChemBIC), Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering