Metal-free hydrosulfonylation of α,β-unsaturated ketones: synthesis and application of γ-keto sulfones

• Published in: RSC advances Vol. 12; no. 55; pp. 35649 - 35654
• Main Authors: Cheng, Xiufang, Wang, Shuo, Wei, Yibo, Wang, Huamin, Lin, Ying-Wu
• Format: Journal Article
• Language: English
• Published: England Royal Society of Chemistry 12.12.2022; The Royal Society of Chemistry
• Subjects: Chemical synthesis; Chemistry; Cycloaddition; Cyclopentene; Functional groups; Ketones; Oxidizing agents; Phosphines; Sulfones
• ISSN: 2046-2069; 2046-2069
• DOI: 10.1039/d2ra06784f

γ-Keto sulfones are versatile building blocks and valuable intermediates in organic synthesis and pharmaceutical chemistry. Motivated by their excellent properties, we herein report a green, convenient, metal-free hydrosulfonylation method for a variety of ynones, vinyl ketones, and sodium sulfinates in the absence of stoichiometric oxidants. This operationally simple protocol provides straightforward and practical access to a wide range of γ-keto sulfones with broad functional group tolerance from easily available starting materials. Moreover, the β,γ-unsaturated keto sulfones could further react with 2,3-butadienoate to generate cyclopentenes in phosphine-mediated [3 + 2] cycloaddition. The methodology features a convenient, mild, efficient, C-S sulfonylation approach without the use of any metal catalysts and stoichiometric oxidants.