Potassium Carbonate Promoted Nucleophilic Addition of Alkenes with Phosphites

Zhenjun Huang; Wei Liu; Sen Li; Yutian Yang; Shengmei Guo; Hu Cai

doi:10.1055/s-0040-1707852

Synlett, Table of Contents

Synlett 2020; 31(13): 1295-1297
DOI: 10.1055/s-0040-1707852

letter

Potassium Carbonate Promoted Nucleophilic Addition of Alkenes with Phosphites

Zhenjun Huang

^aThe Second Clinical Medical College, Nanchang University, Nanchang, 330031, P. R. of China

,

Wei Liu

^aThe Second Clinical Medical College, Nanchang University, Nanchang, 330031, P. R. of China

,

Sen Li

^bDepartment of Chemistry, Nanchang University, Nanchang, 330031, P. R. of China Email: caihu@ncu.edu.cn Email: smguo@ncu.edu.cn

,

Yutian Yang

^cSchool of Pharmacy, Nanchang University, Nanchang, 330031, P. R. of China

,

Shengmei Guo ∗

^bDepartment of Chemistry, Nanchang University, Nanchang, 330031, P. R. of China Email: caihu@ncu.edu.cn Email: smguo@ncu.edu.cn

,

Hu Cai

^bDepartment of Chemistry, Nanchang University, Nanchang, 330031, P. R. of China Email: caihu@ncu.edu.cn Email: smguo@ncu.edu.cn

› Author Affiliations

Abstract

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^◊ These authors contributed equally to this work.

Abstract

A facile hydrophosphonylation of alkenes by phosphites promoted by potassium carbonate was developed. The reaction features include easy handling, environmental friendliness, and avoidance of the use of strong bases. A variety of alkenes are tolerated in this reaction, with moderate to excellent yields.

Key words

potassium carbonate - addition - alkenes - phosphites - hydrophosphonylation

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References

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15 Butyl 3-(Diphenylphosphoryl)propanoate (3a); Typical Procedure A mixture of 1a (0.4 mmol), 2a (0.8 mmol), and K₂CO₃ (0.8 mmol) in DCE (2 mL) was heated at 100 °C under N₂ for 4 h. The mixture was then extracted with DCE (3 × 5 mL) and the combined organic phase was dried (Na₂SO₄), filtered, and concentrated under reduced pressure. The residue was purified by TLC [silica gel, PE–EtOAc (3:1)] to give a colorless liquid; yield: 132 mg (95%). ¹H NMR (400 MHz, CDCl₃): δ = 7.68 (dd, J = 10.9, 7.6 Hz, 4 H), 7.43 (dd, J = 21.7, 6.4 Hz, 6 H), 3.96 (t, J = 6.6 Hz, 2 H), 2.55 (s, 4 H), 1.48 (pent, J = 6.8 Hz, 2 H), 1.25 (hept, J = 7.3 Hz, 2 H), 0.82 (t, J = 7.4 Hz, 3 H). HRMS (ESI): m/z [M + H]⁺ calcd for C₁₉H₂₄O₃P: 331.1458; found: 331.1467.

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