Potassium Carbonate Promoted Nucleophilic Addition of Alkenes with Phosphites

^◊ 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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• 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.