Efficient access to aliphatic esters by photocatalyzed alkoxycarbonylation of alkenes with alkyloxalyl chlorides

Jian-Qiang Chen (), Xiaodong Tu, Qi Tang, Ke Li, Liang Xu, Siyu Wang, Mingjuan Ji, Zhiming Li () and Jie Wu ()
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Jian-Qiang Chen: Taizhou University
Xiaodong Tu: Taizhou University
Qi Tang: Taizhou University
Ke Li: Taizhou University
Liang Xu: Taizhou University
Siyu Wang: Taizhou University
Mingjuan Ji: Taizhou University
Zhiming Li: Fudan University
Jie Wu: Taizhou University

Nature Communications, 2021, vol. 12, issue 1, 1-15

Abstract: Abstract Aliphatic esters are essential constituents of biologically active compounds and versatile chemical intermediates for the synthesis of drugs. However, their preparation from readily available olefins remains challenging. Here, we report a strategy to access aliphatic esters from olefins through a photocatalyzed alkoxycarbonylation reaction. Alkyloxalyl chlorides, generated in situ from the corresponding alcohols and oxalyl chloride, are engaged as alkoxycarbonyl radical fragments under photoredox catalysis. This transformation tolerates a broad scope of electron-rich and electron-deficient olefins and provides the corresponding β-chloro esters in good yields. Additionally, a formal β-selective alkene alkoxycarbonylation is developed. Moreover, a variety of oxindole-3-acetates and furoindolines are prepared in good to excellent yields. A more concise formal synthesis of (±)-physovenine is accomplished as well. With these strategies, a wide range of natural-product-derived olefins and alkyloxalyl chlorides are also successfully employed.

Date: 2021
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DOI: 10.1038/s41467-021-25628-x

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