Catalyst‐ and Substrate‐Dependent Chemodivergent Reactivity of Stabilised Sulfur Ylides with Salicylaldehydes. Issue 12 (6th May 2021)

• Record Type: Journal Article
• Authors: Denisa Bisag, Giorgiana; Ruggieri, Silvia; Fochi, Mariafrancesca; Bernardi, Luca
• Is Part Of: Advanced synthesis & catalysis. Volume 363:Issue 12(2021)
• Page Start: 3053
• Page End: 3059
• Publication Date: 2021-05-06
• Subjects: Sulfur Ylides -- Chemodivergency -- Chromenes -- Dihydrobenzofurans -- Organocatalysis; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202100124
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: Stabilised sulfur ylides are synthetically appealing compounds, which reactivity under Brønsted acid catalysis has been poorly explored. Herein, we report a new catalyst‐ and substrate‐ dependent chemodivergent reaction between stabilised sulfur ylides and salicylaldehydes, leading to the (suprising) formation of 2 H ‐chromenes or dihydrobenzofurans products. Particular attention was set on the unusual mechanisms involved. Two unique reaction routes including two ylide units in the reactions are proposed. These pathways were validated by performing a selectivity switch in some cases, enabled by the modulation of the nucleophilicity of the sulfur ylide, and by the loading of the Brønsted acid catalyst in the reaction. Abstract :