First palladium-catalyzed denitrated coupling of nitroarenes with sulfinates

Tian, Haiyan; Cao, Aijuan; Qiao, Li-Jun; Yu, Ajuan; Chang, Junbiao; Wu, Yangjie

doi:10.1016/j.tet.2014.09.087

Cited by 26 publications

(9 citation statements)

References 40 publications

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“…Yu and Wu reported an interesting palladium-catalyzed synthesis of sulfones by a denitrative coupling of nitroarenes with sulfinic acid salts (Scheme 77). 131…”

Section: Scheme 76mentioning

confidence: 99%

Recent Advances in the Synthesis of Sulfones

2016

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Sulfones are versatile intermediates in organic synthesis and important building blocks in the construction of biological active molecules or functional materials. This review provides a summary of recent developments in the synthesis of sulfones. 1 Introduction 2 Classical Methods and Variants 2.1 Oxidation of Sulfides 2.2 Aromatic Sulfonylation 2.3 Alkylation/Arylation of Sulfinates 2.4 Addition to Alkenes and Alkynes 2.5 Miscellaneous Methods 3 Metal-Catalyzed Coupling Reactions 4 Sulfone Synthesis by C-H Functionalization 5 Sulfur Dioxide Based Three-Component Approaches 6 Biological Synthesis of Sulfones 7 Conclusion

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“…Yu and Wu reported an interesting palladium-catalyzed synthesis of sulfones by a denitrative coupling of nitroarenes with sulfinic acid salts (Scheme 77). 131…”

Section: Scheme 76mentioning

confidence: 99%

Recent Advances in the Synthesis of Sulfones

2016

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“…6−12 Several aromatic electrophiles have been demonstrated as suitable substrates in this transformation, which include (hetero)aryl halides, 8,9 aryl boronic acids, 10 arenediazonium salts, 11 and nitroarenes. 12 Although the progress in this area is significant, further improvements are still needed. For example, aryl chlorides as the cheapest and most abundant aromatic electrophiles are difficult substrates for either Cu-or Pd-catalyzed coupling reaction, 7−9 while higher catalytic loadings (>10 mol % for both copper salt and ligand) are required for a Cu-catalyzed coupling with aryl iodides and bromides.…”

Section: ■ Introductionmentioning

confidence: 99%

A Class of Amide Ligands Enable Cu-Catalyzed Coupling of (Hetero)aryl Halides with Sulfinic Acid Salts under Mild Conditions

et al. 2018

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The amide derived from 4-hydroxy-l-proline and 2,6-dimethylaniline is a powerful ligand for Cu-catalyzed coupling of (hetero)aryl halides with sulfinic acid salts, allowing the formation of a wide range of (hetero)aryl sulfones from the corresponding (hetero)aryl halides at considerably low catalytic loadings. The coupling of (hetero)aryl iodides and sodium methanesulfinate proceeds at room temperature with only 0.5 mol % CuI and ligand, representing the first example for Cu-catalyzed arylation at both low catalytic loading and room temperature.

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“…Our group has recently reported Pd-catalyzed C–C and C–N bond-forming coupling reactions using nitroarenes as electrophiles. , Notably, these reactions proceed via the unprecedented oxidative addition of the Ar–NO 2 bond to Pd(0), where the reduction of the nitro group does not compete. These results inspired us to trap the oxidative adduct with an appropriate hydride source to achieve the single-step denitration.…”

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confidence: 99%

Reductive Denitration of Nitroarenes

2018

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The Pd-catalyzed reductive denitration of nitroarenes has been achieved via a direct cleavage of the C-NO bonds. The catalytic conditions reported exhibit a broad substrate scope and good functional-group compatibility. Notably, the use of inexpensive propan-2-ol as a mild reductant suppresses the competitive formation of anilines, which are normally formed by other conventional reductions. Mechanistic studies have revealed that alcohols serve as efficient hydride donors in this reaction, possibly through β-hydride elimination from palladium alkoxides.

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First palladium-catalyzed denitrated coupling of nitroarenes with sulfinates

Cited by 26 publications

References 40 publications

Recent Advances in the Synthesis of Sulfones

Recent Advances in the Synthesis of Sulfones

A Class of Amide Ligands Enable Cu-Catalyzed Coupling of (Hetero)aryl Halides with Sulfinic Acid Salts under Mild Conditions

Reductive Denitration of Nitroarenes

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