Insertion of sulfur dioxide <i>via</i> a radical process: an efficient route to sulfonyl compounds

Qiu, Guanyinsheng; Zhou, Kaida; Gao, Liang; Wu, Jie

doi:10.1039/c7qo01073g

Cited by 306 publications

(68 citation statements)

References 105 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Since the submission of this review several new methods for the synthesis of molecules containing sulfonyl‐functionalities and one review article have been reported in the literature, highlighting the tremendous activity in this research area …”

Section: Discussionmentioning

confidence: 99%

Radicals and Sulfur Dioxide: A Versatile Combination for the Construction of Sulfonyl‐Containing Molecules

Hofman

Liu

Manolikakes

2018

Chemistry A European J

251

View full text Add to dashboard Cite

Molecules containing a sulfonyl functionality, such as sulfones, sulfonyl chlorides or sulfonamides play an important role in organic chemistry and have found widespread application, especially in the construction of biologically active compounds. Recently, methods for the synthesis of the sulfonyl moiety utilizing sulfur dioxide as a key building block have received considerable attention. In this context, radical-based transformations with sulfur dioxide have emerged as a new and attractive approach for the construction of the sulfonyl functional group. This short review highlights recent advances in the use of sulfur dioxide in radical reactions and covers the historical background, which forms the basis for these current progresses. Limitations of the existing methods and potential further developments will be discussed.

show abstract

Section: Discussionmentioning

confidence: 99%

Radicals and Sulfur Dioxide: A Versatile Combination for the Construction of Sulfonyl‐Containing Molecules

Hofman

Liu

Manolikakes

2018

Chemistry A European J

251

View full text Add to dashboard Cite

show abstract

“…In the past few years, insertion of sulfur dioxide via radical processes has been developed rapidly for the synthesis of sulfonyl compounds. [13,14] Generally, DABCO·(SO 2 ) 2 [15] or inorganic sulfites [16] are used as the sulfur dioxide surrogates. Various carbon radical precursors [17][18][19] have been utilized in the transformations.…”

Section: Introductionmentioning

confidence: 99%

Three‐Component Reaction of Potassium Alkyltrifluoroborates, Sulfur Dioxide and Allylic Bromides under Visible‐Light Irradiation

Xie

et al. 2019

Asian J Org Chem

Self Cite

View full text Add to dashboard Cite

Diverse allylic sulfones are generated through a three-component reaction of potassium alkyltrifluoroborates, sulfur dioxide and allylic bromides in the presence of 9mesityl-10-methyl acridinium perchlorate under visible light irradiation at room temperature. This transformation proceeds efficiently, and a broad reaction scope is demonstrated with good functional groups tolerance. This reaction is initiated by the treatment of potassium alkyltrifluoroborate under visible-light irradiation in the presence of a photocatalyst, leading to alkyl radical. This alkyl radical intermediate is trapped by sulfur dioxide to provide alkylsulfonyl radical, which then undergoes further transformation to afford the corresponding allylic sulfone. Results and DiscussionAt the outset, a three-component reaction of 3-bromo-2methylprop-1-ene 1 a, potassium cyclopentyltrifluoroborate 2 a, and DABCO·(SO 2 ) 2 was carried out as a model to explore the optimal reaction parameters under visible light irradiation. The results are provided in Table 1. Initially, the reaction was [a] S. Scheme 1. A proposed radical strategy for the synthesis of allylic sulfones.

show abstract

“…It summarizes the literature data, mainly from 2000 to 2018. Radical insertion of sulfur dioxide into organic molecules with the formation of S–N bonds has already been summarized and is not included in this review. The review is divided into chapters in accordance with the classes of compounds synthesized: firstly the synthesis of linear molecules is described, after which heterocyclization reactions and formation of structures containing more than two heteroatoms in succession are discussed.…”

Section: Introductionmentioning

confidence: 99%

Oxidative Coupling with S–N Bond Formation

2018

View full text Add to dashboard Cite

Oxidative strategies are a powerful tool in organic synthesis for the formation of heteroatom–heteroatom, carbon–heteroatom, and carbon–carbon bonds. Among these processes the reactions of oxidative S–N bond formation deserve considerable interest as convenient, effective, and environmentally friendly alternatives to existing methods for the synthesis of a great variety of organic compounds widely used in organic and medicinal chemistry. These transformations take place through the interaction of S‐ and N‐reagents and an oxidant, by radical or ionic mechanisms. Sulfinic acids and their salts, thiols, sulfonyl hydrazides, and thiosulfonates are generally used as S‐reagents; aliphatic and aromatic amines are usually applied as N‐reagents. The role of the oxidant mostly lies in the oxidation of the S‐reagent, after which the formed active species reacts with the N‐reagent to result in the S–N coupling product. There are two versions of oxidative S–N coupling processes: the intermolecular variant opens simple pathways to sulfen‐, sulfin‐, and sulfonamides, sulfenyl‐ and sulfoximines, sulfanes, and sulfur diimides, whereas the intramolecular one leads to the formation of various heterocycles. Of the major problems associated with successful performance of oxidative S–N coupling reactions, the first relates to the search for coupling partners that will work together to form a new bond under oxidative conditions. The second is the choice of a suitable oxidative system that will not overoxidize starting compounds. That is why mild oxidants, such as hypervalent iodine compounds and copper salts and complexes, are generally applied in these processes. This is the first exhaustive review relating to achievements in oxidative transformations involving S–N bond formation. It summarizes 134 references, mainly from 2000 to 2018, and is divided into chapters according to the classes of compounds synthesized.

show abstract

Insertion of sulfur dioxide via a radical process: an efficient route to sulfonyl compounds

Abstract: This review is focused on the recent advances in the chemistry of sulfur dioxide fixation through a radical process. Diverse sulfonyl compounds can be obtained efficiently under mild conditions.

Cited by 306 publications

References 105 publications

Radicals and Sulfur Dioxide: A Versatile Combination for the Construction of Sulfonyl‐Containing Molecules

Radicals and Sulfur Dioxide: A Versatile Combination for the Construction of Sulfonyl‐Containing Molecules

Three‐Component Reaction of Potassium Alkyltrifluoroborates, Sulfur Dioxide and Allylic Bromides under Visible‐Light Irradiation

Oxidative Coupling with S–N Bond Formation

Contact Info

Product

Resources

About