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Synthesis 2019; 51(19): 3667-3674
DOI: 10.1055/s-0039-1690105
DOI: 10.1055/s-0039-1690105
paper
Bu4NI-Catalyzed C–C Bond Cleavage and Oxidative Esterification of Allyl Alcohols with Toluene Derivatives
The authors gratefully acknowledge financial support from National Key Research and Development Program of China (2017YFB0102900) and State Key Laboratory of Applied Organic Chemistry, Lanzhou University. This work is also sponsored by Natural Science Foundation of Shanghai (18ZR1413900) and Shanghai Pujiang Program (17PJD016).Further Information
Publication History
Received: 26 April 2019
Accepted after revision: 10 June 2019
Publication Date:
16 July 2019 (online)
§ These authors contributed equally to this work.
Abstract
A novel oxidative esterification of 1-arylprop-2-en-1-ols with toluene derivatives catalyzed by tetrabutylammonium iodide (TBAI) is reported. The optimization of the reaction conditions illustrates that each of experiment parameters including the catalyst, solvent, and oxidant is significant for present oxidative functionalization. This metal-free protocol has a broad substrate scope including the halogen groups for further functionalization and enriches the reactivity profile of allyl alcohol and toluene derivatives. In addition, this protocol represents a new transformation of allyl alcohol involving C–C bond cleavage and C–O bond forming.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690105.
- Supporting Information
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