Citation: Zhihua Wang, Xiang-Zhao Zhu, Xinglei He, Chen-Xu Gong, Wang-Fu Liang, Wenfeng Wang, Yuqi Lin, Ke-Yin Ye. Deoxygenative hydrohalogenation of propargyl alcohols: Regio- and stereoselective synthesis of unsaturated distal dihalides[J]. Chinese Chemical Letters, ;2025, 36(12): 111067. doi: 10.1016/j.cclet.2025.111067 shu

Deoxygenative hydrohalogenation of propargyl alcohols: Regio- and stereoselective synthesis of unsaturated distal dihalides

Zhihua Wang ^a ,
Xiang-Zhao Zhu ^a ,
Xinglei He ^a ,
Chen-Xu Gong ^a ,
Wang-Fu Liang ^a ,
Wenfeng Wang ^a ,
Yuqi Lin ^a ,
Ke-Yin Ye ^{a, b, *,}

a.
Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), College of Chemistry, Fuzhou University, Fuzhou 350108, China
b.
School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, China

kyye@fzu.edu.cn

Received Date: 12 December 2024
Revised Date: 8 March 2025
Accepted Date: 11 March 2025
Available Online: 13 March 2025

Figures(8)

In contrast to the well-established synthetic protocols for monoalkenyl halides, a general approach to access diverse distal bisalkenyl halides with high synthetic fidelity has not yet been established, which are found in various biologically active natural products and may also serve as useful building blocks in organic synthesis. We herein report a cobalt-catalyzed regio- and stereoselective deoxygenative hydrohalogenation of propargyl alcohols to access Z-configurated alkenyl halides and the analogous distal bisalkenyl chlorides, bromides, and iodides. Mechanistic investigation suggests that the regio- and stereoselective stepwise hydrogenation of in situ generated chloroallenes is the key step wherein the commercially available halodimethylsilane, or a surrogate combination of hydrosilane and halosilane, serves both as the hydrogen and chlorine sources.
- Cobalt catalysis,
- Halosilane,
- Organohalides,
- Propargyl alcohols,
- Regioselectivity
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