Bifunctional iron-catalyzed alkyne Z-selective hydroalkylation and tandem Z-E inversion via radical molding and flipping

Yongqiang Zhang, Dongmin Fu, Ziyang Chen, Rongqi Cui, Wenlong He, Hongyao Wang, Jiajin Chen, Yufei Chen, Shi-Jun Li, Yu Lan (), Chunying Duan and Yunhe Jin ()
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Yongqiang Zhang: Dalian University of Technology
Dongmin Fu: Zhengzhou University
Ziyang Chen: Dalian University of Technology
Rongqi Cui: Dalian University of Technology
Wenlong He: Dalian University of Technology
Hongyao Wang: Dalian University of Technology
Jiajin Chen: Dalian University of Technology
Yufei Chen: Dalian University of Technology
Shi-Jun Li: Zhengzhou University
Yu Lan: Zhengzhou University
Chunying Duan: Nanjing University
Yunhe Jin: Dalian University of Technology

Nature Communications, 2024, vol. 15, issue 1, 1-13

Abstract: Abstract The challenging synthesis of thermodynamic-unfavored cis-olefins through catalytic cross-coupling reactions requires the synergistic interaction of substrate-activating units and configuration-regulating catalysts. Successfully hitting these two birds with one stone, we herein develop a convenient photoredox access to Z-alkenes from alkynes and light alkanes with a bifunctional iron-catalyzed system possessing both C(sp3)−H activation and configuration-controlling abilities. The protocol exhibits 100% atom utilization, mild conditions, a broad substrate scope, and compatibility with multitudinous functional groups. The detailed reaction mechanism and the origin of geometry regulation are well investigated by experimental and computational studies. Progressively, a catalytic amount of diaryl disulfides is introduced for consecutive photoinduced Z−E isomerization via reversible radical addition and flipping. Big steric hindrance substituents assembled on the disulfide emerge necessity for suppressing double-bond migration. This tandem strategy paves a promising way for stereoselective alkene construction and will bring significant inspiration for the development of transition metal photocatalysis.

Date: 2024
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DOI: 10.1038/s41467-024-53021-x

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