Lone pair-π interaction induced regioselective sulfonation of ethers under light irradiation

Abstract

Non-covalent interactions are of significance in supramolecular chemistry and biochemistry, while synthetic procedures driven by these weak interactions remain challenging and rare. Inspired by the lone pair-π interaction presence in the Z-DNA structure, a light-induced regioselective sulfonation of ethers taking advantage of the lone pair-π interaction between the oxygen of ethers and sulfonyl chlorides has been disclosed. Moreover, this strategy is also applicable to the sulfonation of aniline derivatives. Features of the methods include readily accessible starting materials, high atom-economy, green and photocatalyst-free conditions and broad functional group tolerance. Mechanism studies suggest that the lone pair-π interaction plays an important role to initiate the transformation.

Keywords

• Non-covalent interactions
• Lone-pair-π interactions
• Sulfonyl radical
• Photocatalysis
• Ethers