Dioxygen concentration-dependent selective hydroxysulfonylation of olefins by rose bengal-sensitized photocatalysis

• DOI: 10.1039/d3ob01162c
• Publication Date: 2023-09-15T09:21:38Z
• Authors: Navin Yadav; Soumen Payra; Parag Tamuly; Jarugu Narasimha ...
• Keywords: Sulfonyl; Rose bengal

The synthesis of β-hydroxysulfones selectively in preference to β-ketosulfones by dye-sensitized photocatalysis is demonstrated employing inexpensive and readily available olefins sulfonyl hydrazides/N-hydroxy sulfonamides the presence oxygen. facile hydroxysulfonylation reaction, which involves use rose bengal (RB) as a photocatalyst dioxygen an oxidant, permits access secondary tertiary good excellent isolated yields at rt compatible with aryl, heteroaryl alkyl hydrazides. Mechanistically, radicals are generated cascade redox reactions, set off RB, between hydrazide dioxygen. Attack on followed oxygenation radical intermediates leads products without requirement metal catalyst/additive/reductant/base, conforming tenets sustainable chemistry. It shown that formations proceed concurrently through two different routes outcome crucially dependent oxygen concentration former being formed predominantly under atmosphere, feature heretofore unprecedented best our knowledge.