Visible-light mediated sulfonylation of thiols <i>via</i> insertion of sulfur dioxide

Nair, Akshay M.; Kumar, Shreemoyee; Halder, Indranil; Volla, Chandra M. R.

doi:10.1039/c9ob01040h

Cited by 44 publications

(23 citation statements)

References 59 publications

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“…Akshay M. Nair and co‐workers investigated aryl sulfonylation of thiols by treating thiophenol & DABCO ⋅ (SO 2 ) 2 with aryl diazonium salt at room temperature under photocatalytic conditions using eosin Y as a photocatalyst (Scheme 47). [72] Thiophenols bearing various functional groups such as methyl, methoxy, isopropyl, halogens, and naphthalene furnished the desired products in good yields under the optimized conditions. Notably, aliphatic thiols were also effective for this transformation and gave the expected products in good yields.…”

Section: C−s Bond Formationmentioning

confidence: 98%

Aryldiazonium Salts in Photoredox Catalysis – Recent Trends

et al. 2021

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Aryl diazonium salts are an important class of organic compounds that are now widely used as arylating agents in photoredox catalysis owing to their lower redox potential, broad substrate scope, and atom economy. They have successfully been used in many interesting organic transformations to introduce an aryl group. They serve as good alternatives for aryl halides and other aryl organometallic reagents primarily used as aryl group surrogates. New reactions using aryl diazonium salts are continually emerging, and in this review, we have highlighted some recent developments in photoredox arylations and their applications. 4.3. Oxy-Arylation of Alkynes for the Synthesis of Benzofuran 4.4.

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Section: C−s Bond Formationmentioning

confidence: 98%

Aryldiazonium Salts in Photoredox Catalysis – Recent Trends

et al. 2021

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“…In 2019, Volla and co-workers reported a protocol for the synthesis of thiosulfonates, via the three-component coupling of aryl diazonium salts, SO 2 , and thiols, mediated by visible-light photocatalysis ( Scheme 246 ). 640 Green-light irradiation of EY in the presence of thiol, aryl diazonium salt, and DABSO—the charge-transfer complex formed between DABCO and sulfur dioxide 641 —afforded 34 examples of thiosulfonate products in 54–89% yield. The authors demonstrated a wide scope of thiols, including thiophenols containing EWGs ( 246.1 ) and EWGs ( 246.2 ).…”

Section: S -Centered Radical Generation From S–h Bonds Through Photochemical and Electrochemical Pcet Processesmentioning

confidence: 99%

Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis

et al. 2021

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We present here a review of the photochemical and electrochemical applications of multi-site proton-coupled electron transfer (MS-PCET) in organic synthesis. MS-PCETs are redox mechanisms in which both an electron and a proton are exchanged together, often in a concerted elementary step. As such, MS-PCET can function as a non-classical mechanism for homolytic bond activation, providing opportunities to generate synthetically useful free radical intermediates directly from a wide variety of common organic functional groups. We present an introduction to MS-PCET and a practitioner’s guide to reaction design, with an emphasis on the unique energetic and selectivity features that are characteristic of this reaction class. We then present chapters on oxidative N–H, O–H, S–H, and C–H bond homolysis methods, for the generation of the corresponding neutral radical species. Then, chapters for reductive PCET activations involving carbonyl, imine, other X=Y π-systems, and heteroarenes, where neutral ketyl, α-amino, and heteroarene-derived radicals can be generated. Finally, we present chapters on the applications of MS-PCET in asymmetric catalysis and in materials and device applications. Within each chapter, we subdivide by the functional group undergoing homolysis, and thereafter by the type of transformation being promoted. Methods published prior to the end of December 2020 are presented.

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“…This reaction proceeds via a radical-radial cross-coupling reaction promoted by an eosin Y photocatalyst under irradiation of visible light. 52…”

Section: Reviewmentioning

confidence: 99%