Efficient reduction of sulfoxides with NaHSO 3 catalyzed by I 2

Abbasi, Mohammad; Mohammadizadeh, Mohammad R.; Moradi, Zahra

doi:10.1016/j.tetlet.2015.10.035

Cited by 24 publications

(12 citation statements)

References 57 publications

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“…Other reagents such as sulfur reagents, phosphorus reagents, were also used for deoxygenation. On other side, different catalytic systems have been employed for the deoxygenation of sulfoxide viz., B(C 6 F 5 ) 3 /hydrosilanes, I 2 , Zn(OTf) 2 /boranes, ruthenium nanoparticles, silane/MoO 2 Cl 2 , oxo complexes, gold nanoparticles, SOCl 2 , and Fe powder, etc.…”

Section: Methodsmentioning

confidence: 99%

I₂/K₂S₂O₈: An Unprecedented Deoxygenating System for N‐Oxides and Sulfoxides

2019

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A novel and efficient metal‐free approach has been disclosed for the deoxygenation of amine N‐oxides to amines and sulfoxides to corresponding sulfides using the green and economical reagent I2/K2S2O8. Deoxygenation of pyridine N‐oxide, quinoline N‐oxide, N,N‐dialkylaniline N‐oxides, trialkylamine N‐oxides and aryl sulfoxides have been achieved in excellent yields. This method has been proven to be applicable to a wide range of substrates. A broad range of functional groups were well tolerated in this reaction system.

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Section: Methodsmentioning

confidence: 99%

I₂/K₂S₂O₈: An Unprecedented Deoxygenating System for N‐Oxides and Sulfoxides

2019

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“…Actually, the existing methods to reduce sulfoxides can be divided in three categories: hydrogenations (Scheme a), when the reducing agent is molecular hydrogen (produced in situ or inserted), are usually catalyzed by expensive transition‐metal catalysts and are impractical with unsaturated or reducible functions; reductions, (Scheme b) when the reducing agent is a hydride, usually a silane, and catalysts include boron compounds or transition metals; the functional group tolerance for reductions is fairly poor since other electrophilic groups react with the reductive mixture. Finally, deoxygenations, (Scheme c), which are promoted by the activation of a sulfoxide with strong electrophiles, need low temperatures and, in most cases, stoichiometric amounts of base. An alternative photocatalytic deoxygenation was described very recently .…”

Section: Introductionmentioning

confidence: 99%

Electrophilic Chlorine from Chlorosulfonium Salts: A Highly Chemoselective Reduction of Sulfoxides

Acosta-Guzmán

Mahecha-Mahecha

Gamba‐Sánchez

2020

Chemistry A European J

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Herein, we describe a selective late‐stage deoxygenation of sulfoxides based on a novel application of chlorosulfonium salts and demonstrate a new process using these species generated in situ from sulfoxides as the source of electrophilic chlorine. The use of highly nucleophilic 1,3,5‐trimethoxybenzene (TMB) as the reducing agent is described for the first time and applied in the deoxygenation of simple and functionalized sulfoxides. The method is easy to handle, economic, suitable for gram‐scale operations, and readily applied for poly‐functionalized molecules, as demonstrated with more than 45 examples, including commercial medicines and analogues. We also report the results of competition experiments that define the more reactive sulfoxide and we present a mechanistic proposal based on substrate and product observations.

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“…in the presence of 5 mol% of ionic-liquid-molybdenum complexes in ionic liquid/toluene (21), NaHSO 3 (1.1 eq. )/10 mol% of I 2 in chloroform (22), catecholborane (2 eq. )/5 mol% of Rh catalyst in C 6 D 6 (23), pinacol (2 eq.…”

Section: Introductionmentioning

confidence: 99%