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Synthesis 2023; 55(10): 1543-1552
DOI: 10.1055/a-2017-6065
DOI: 10.1055/a-2017-6065
paper
Transition-Metal-Free Dehydrogenative Cyclization via α-Csp3–H Activation of Ethers and Thioethers
This research was funded by the Science and Engineering Research Board (SERB, DST, India; Core Research Grant No. CRG/2021/006717). KM and HMB thank the Council of Scientific and Industrial Research, India (CSIR) for their fellowships.
Abstract
We report herein the tetraethylammonium bromide catalyzed intramolecular oxidative cyclization of O- or S-alkylated salicylic or thiosalicylic acid derivatives to access 4H-benzo[d][1,3]dioxin-4-ones or 4H-benzo[d][1,3]oxathiin-4-ones, respectively. The oxidative cyclization of salicylic acid derivatives proceeds through a radical pathway at 110 °C. In contrast, the cyclization of the thiosalicylic acids proceeds smoothly at room temperature via an ionic pathway. Notably, the overall reactions are fast, completed within short reaction times, furnishing the products in high yields and with smooth formation of quaternary carbon centers.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2017-6065.
- Supporting Information
- CIF File
Publication History
Received: 02 November 2022
Accepted after revision: 23 January 2023
Accepted Manuscript online:
23 January 2023
Article published online:
27 February 2023
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