Citation: Sa-Na Yang, Shao-Han Sun, Chang-Hui Liu, Xiang-Ting Min, Boshun Wan, Ding-Wei Ji, Qing-An Chen. Ni-catalyzed regiodivergent hydrophosphorylation of enynes[J]. Chinese Chemical Letters, ;2023, 34(6): 107914. doi: 10.1016/j.cclet.2022.107914 shu

Ni-catalyzed regiodivergent hydrophosphorylation of enynes

Sa-Na Yang ^{a, b} ,
Shao-Han Sun ^{a, b} ,
Chang-Hui Liu ^{a, b} ,
Xiang-Ting Min ^a ,
Boshun Wan ^{a, b} ,
Ding-Wei Ji ^{a, *,} ,
Qing-An Chen ^{a, b, *,}

a.
Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China
b.
University of Chinese Academy of Sciences, Beijing 100049, China

dingweiji@dicp.ac.cn

qachen@dicp.ac.cn

Received Date: 19 August 2022
Revised Date: 11 October 2022
Accepted Date: 17 October 2022
Available Online: 22 October 2022

Figures(6)

A regiodivergent hydrophosphorylation of enynes with phosphites has been developed using earth-abundant nickel catalyst. The manipulation of regioselectivity can be achieved by regulating the insertion order of alkyne bonds with (RO)₂P(O)–Ni–H or R₂P(O)O–Ni–H species, respectively. Under the Ni/Xantphos catalysis, 4,1-hydrophosphorylation is selectively obtained while the adding of acid can promote reactions towards 1,2-addition. By employing an additional Pd–H catalysis, 2,1-hydrophosphorylation is also an accessible task in one-pot reaction. Mechanistic studies and analysis have also been performed to interpret the origin of the regioselective regulation. This work highlights the arts in accessing different regioisomers by diverting common elementary reaction steps.
- Regiodivergent,
- Hydrophosphorylation,
- Nickel catalysis,
- Enynes
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