Citation: Jian Han, Li-Li Zeng, Qin-Yu Fei, Yan-Xiang Ge, Rong-Hui Huang, Fen-Er Chen. Recent advances in remote C(sp³)–H functionalization via chelating group-assisted metal-catalyzed chain-walking reaction[J]. Chinese Chemical Letters, ;2024, 35(11): 109647. doi: 10.1016/j.cclet.2024.109647 shu

Recent advances in remote C(sp³)–H functionalization via chelating group-assisted metal-catalyzed chain-walking reaction

Jian Han ^{a, c, *,} ,
Li-Li Zeng ^a ,
Qin-Yu Fei ^a ,
Yan-Xiang Ge ^a ,
Rong-Hui Huang ^{a, *,} ,
Fen-Er Chen ^{a, b, **,}

a.
School of Pharmacy, Changzhou University, Changzhou 213164, China
b.
Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University, Shanghai 200433, China
c.
Shenzhen Research Institute of Nanjing University, Shenzhen 518057, China

^**

xhj@cczu.edu.cn

ronghuihuang@cczu.edu.cn

rfchen@fudan.edu.cn

Received Date: 4 December 2023
Revised Date: 22 January 2024
Accepted Date: 6 February 2024
Available Online: 11 February 2024

Figures(21)

Aliphatic C(sp³)–H moieties are ubiquitous in numerous organic compounds. Direct functionalization of inert C(sp³)–H bonds is a powerful and straightforward approach for the efficient construction of diverse carbon–carbon or carbon–heteroatom bonds. Chelating group directed metal-catalyzed remote functionalization of readily available alkenes has emerged as an appealing strategy for rapidly accessing various value-added aliphatic molecules. With the aid of directing groups, various α-, β- and γ-functionalized alkanes could be synthesized smoothly with excellent regioselectivity. The preferred formation of a stable five- or six-membered metallacycle intermediate terminates the chain-walking at a specific methylene site, which serves as the driving force for excellent site-selective migratory functionalization. This review herein is aimed at summarizing the recent progress on the metal-catalyzed regiodivergent functionalization of unactivated alkenes by merging alkene isomerization and cross-coupling with the assistance of directing auxiliary. Last but not least, the current situations and future directions in this field are highlighted and discussed.
- Chelating group,
- Chain-walking,
- Regiodivergent,
- Unactivated alkenes,
- C(sp³)–H functionalization,
- Transition-metal catalysis
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Recent advances in remote C(sp3)–H functionalization via chelating group-assisted metal-catalyzed chain-walking reaction

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Recent advances in remote C(sp³)–H functionalization via chelating group-assisted metal-catalyzed chain-walking reaction