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Synlett 2020; 31(13): 1295-1297
DOI: 10.1055/s-0040-1707852
letter
© Georg Thieme Verlag Stuttgart · New York

Potassium Carbonate Promoted Nucleophilic Addition of Alkenes with Phosphites

Zhenjun Huang
a   The Second Clinical Medical College, Nanchang University, Nanchang, 330031, P. R. of China
,
Wei Liu
a   The Second Clinical Medical College, Nanchang University, Nanchang, 330031, P. R. of China
,
Sen Li
b   Department of Chemistry, Nanchang University, Nanchang, 330031, P. R. of China   Email: caihu@ncu.edu.cn   Email: smguo@ncu.edu.cn
,
Yutian Yang
c   School of Pharmacy, Nanchang University, Nanchang, 330031, P. R. of China
,
Shengmei Guo  ∗
b   Department of Chemistry, Nanchang University, Nanchang, 330031, P. R. of China   Email: caihu@ncu.edu.cn   Email: smguo@ncu.edu.cn
,
Hu Cai
b   Department of Chemistry, Nanchang University, Nanchang, 330031, P. R. of China   Email: caihu@ncu.edu.cn   Email: smguo@ncu.edu.cn
› Author AffiliationsWe thank the National Natural Science Foundation of China (21861024, 21571094, 21571094) for financial support.
Further Information

Publication History

Received: 12 December 2019

Accepted after revision: 08 May 2020

Publication Date:
18 June 2020 (online)

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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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707852.
  • Supporting Information
 

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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.