Direct Synthesis of Sulfinamides by the Copper‐Catalyzed Electrophilic Amidation of Sulfenate Anions

Dai, Qiang; Zhang, Junliang

doi:10.1002/adsc.201701510

Cited by 36 publications

(19 citation statements)

References 71 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Zhang and co-workers [32] developed an effective and reliable method for copper-catalyzed electrophilic amination of sulfonate under mild conditions [Eq. (17)].…”

Section: S-n Formation Reactions Based On Sulfonyl Groupmentioning

confidence: 99%

“…Raju and co-workers [48] successfully developed a mild, basefree method for the S-P bond formation using odorless, airstable sulfonylhydrazides as sulfur source and H-phosphonates as phosphine source [Eq. (32)]. The protocol was compatible with various functional groups, affording a series of thiophosphate derivatives in good to high yields.…”

Section: S-p Formation Reactions Based On Sulfonyl Groupmentioning

confidence: 99%

See 1 more Smart Citation

Recent Advances in Sulfur‐Centered S–X (X = N, P, O) Bond Formation Catalyzed by Transition Metals

Peng

Dong

2020

Eur J Org Chem

View full text Add to dashboard Cite

Compounds containing S–X (X = N, P, O) bonds are commonly found in organic synthesis, medicinal chemistry and pesticide chemistry. The use of transition metal catalysts enables the development of more efficient and environmentally friendly synthetic processes. The reaction strategy between sulfur sources (such as sulfenyl or sulfonyl compounds) and organic substrates (such as amines, phosphites, or alcohols) is one of the most important methods to give S–X (X = N, P, O) bond. Herein, we summarize the recent research progress on the S–X (X = N, P, O) bond formation catalyzed by transition metals, mainly starting from sulfur sources containing sulfenyl or sulfonyl group.

show abstract

“…Zhang and co-workers [32] developed an effective and reliable method for copper-catalyzed electrophilic amination of sulfonate under mild conditions [Eq. (17)].…”

Section: S-n Formation Reactions Based On Sulfonyl Groupmentioning

confidence: 99%

Section: S-p Formation Reactions Based On Sulfonyl Groupmentioning

confidence: 99%

Recent Advances in Sulfur‐Centered S–X (X = N, P, O) Bond Formation Catalyzed by Transition Metals

Peng

Dong

2020

Eur J Org Chem

View full text Add to dashboard Cite

show abstract

“…Through the action of the CuI/bpy system, sulfinamides 126 were also obtained from tert ‐butyl esters of β‐sulfinic acids 124 and N ‐benzoyloxyamines 125 (Scheme ) …”

Section: Synthesis Of Sulfenamides and Sulfinamidesmentioning

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

“…Sulfenate chemistry also represents a growing area of organic methodology, with major contributions directed toward organocatalysis along with enantioselective, and diastereoselective sulfoxide synthesis In addition, the recently reported conversion to sulfinamides and copper‐catalyzed sulfoxidation of benzylic C–H bonds reflect novel modes of sulfenate reactivity. As prochiral entities, sulfenate anions may succumb to S‐functionalization to give either of two sulfoxide configurations.…”

Section: Introductionmentioning

confidence: 99%

A Computational Determination of the Origins of Diastereoselective Alkylations of a Cysteinesulfenate Anion

Schwan

2018

Eur J Org Chem

View full text Add to dashboard Cite

Sulfenic acid anions (RSO–) represent an untapped functional group for the formation of sulfoxides and other organic compounds. Their stereoselective alkylation is an important component of this chemistry, but factors governing reaction outcomes are not fully understood. The current study uses Density Functional Theory methods to break down the influencing roles of substituents attached to 2‐aminoethanesulfenate. The lithium counterion can be coordinated to pendant ester or carbamate carbonyl groups, whereas the sulfenate oxygen readily participates in hydrogen bonding with proximal hydrogen atoms of the (protected) amino group. A Moc‐protected, ester substituted, 2‐aminoethanesulfenate adopts both lithium coordination and hydrogen bonding in the lowest energy form and demonstrates stereoselective methylation and benzylation consistent with experiments from the literature.

show abstract

Direct Synthesis of Sulfinamides by the Copper‐Catalyzed Electrophilic Amidation of Sulfenate Anions

Cited by 36 publications

References 71 publications

Recent Advances in Sulfur‐Centered S–X (X = N, P, O) Bond Formation Catalyzed by Transition Metals

Recent Advances in Sulfur‐Centered S–X (X = N, P, O) Bond Formation Catalyzed by Transition Metals

Oxidative Coupling with S–N Bond Formation

A Computational Determination of the Origins of Diastereoselective Alkylations of a Cysteinesulfenate Anion

Contact Info

Product

Resources

About