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Abstract
Allylic sulfoxides are ubiquitous in medicine and catalysis. Chemo-selective synthesis of allyl-aryl sulfoxides are challenging as competitive isomerization, over oxidation of allylic C-H as well as sulfur. Herein, we have accomplished an unprecedented, metal-free one-pot protocol for the exclusive synthesis of allyl-aryl sulfinyls from Morita–Baylis–Hillman allyl bromides and thiols under visible light photocatalysis through a radical process. The highlight of this process is the selective and controlled oxidation of in situ formed allyl-aryl sulfides by merging sub-stoichiometric oxidizing agent TEMPO and visible light photocatalysis where overoxidation was completely excluded. This approach provides an efficient one-step access to biologically relevant and synthetically important molecules.
Supplementary materials
Title
One-pot Chemo Selective Aerobic Cascade Synthesis of Allyl-Aryl Sulfoxides Enabled by Photoinduced Na2 - Eosin Y and TEMPO
Description
For the first time, we have accomplished a simple one-pot visible light mediated protocol for the selective and controlled synthesis of a library of allyl-aryl sulfinyls from Morita–Baylis–Hillman allyl-aryl bromide derivatives and thiols under aerobic condition. Eosin Y disodium salt is used as a photocatalyst, and TEMPO is used as a sub-stochiometric oxidizing agent. A plausible radical mechanism is proposed with adequate supporting evidence by analysing the crude HRMS and control experiments. We have also demonstrated the application of the developed methodology for the synthesis of biologically relevant compounds with anticancer and anti-abnormal cell proliferation agent against the NLRP3 inflammasome. In particular, the approach provides efficient one-step access to biologically relevant and synthetically important molecules.
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