Recent trends in the synthesis and applications of β-iodovinyl sulfones: a decade of progress

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(13), С. 2492 - 2509

Опубликована: Янв. 1, 2024

Over the past decade, there has been exponential growth in vicinal iodosulfonylation of alkynes using sulfonyl and iodide reactants. This review highlights recent developments β-iodovinyl sulfones their applications organic synthesis.

Язык: Английский

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Cu-Catalyzed biheterocyclization along with sulfonyl remote migration: Access to Marinoquinoline alkaloids and 4-sulfonyl pyrrolo[2,3-c]quinolines

Chinese Chemical Letters, Год журнала: 2025, Номер unknown, С. 110915 - 110915

Опубликована: Фев. 1, 2025

Язык: Английский

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Palladium-Catalyzed Intermolecular 1,3-Dienylation of Propargyl Esters Involving the Insertion of SO₂

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Фев. 20, 2025

A palladium-catalyzed three-component 1,3-dienylation of propargylic esters with DABSO and aryl iodides has been developed. This novel reductive cross-coupling reaction produces 2-sufonylated 1,3-dienes as single products in the presence metal Mn high regio- chemoselectivities. Control experiments demonstrated that transformation may undergo a radical process.

Язык: Английский

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Lewis Acid-Mediated Domino Glycosylation/Cyclization of Substituted Glycals: A Stereoselective Route Toward the Synthesis of 1,2-Annulated C-Glycosides

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 14, 2025

Annulated C-glycosides are widely recognized for their natural abundance and diverse bioactivity. Traditional synthesis emphasizes stereoselective α/β C-glycoside formation, but efficiently engaging both reactive carbons of glycosyl donors remains challenging. This study introduces a novel domino sequence using substituted glycals β-naphthols under Lewis acid catalysis, generating glycosylated intermediates that undergo cascade reactions to yield annulated 1,2-C-glycosides. The method features broad substrate scope, mild conditions, versatility. Notably, annulation type varies with glycals, yielding [3 + 2] or 3] fused pyran systems. Control experiments DFT calculations provide mechanistic insights into substrate-specific product formation.

Язык: Английский

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Synthesis of Sulfonylthiophenes through [3+2] Cycloaddition of Pyridinium 1,4-Zwitterionic Thiolates with (E)-β-Iodovinyl Sulfones or Bromoallylsulfones

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Май 7, 2025

A novel metal-free [3+2] cycloaddition strategy involving (E)-β-iodovinyl sulfones or bromoallylsulfones and pyridinium 1,4-zwitterionic thiolates for the efficient synthesis of sulfonylthiophenes is presented. This method exhibits good substrate tolerance, catalysis, easily prepared bench-stable substrates. The findings highlight a practical protocol accessing sulfonyl-substituted thiophenes with significant biological chemical relevance, serving as an alternative to traditional metal catalysis oxidation aryl/heteroaryl sulfides.

Язык: Английский

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Recent Advances in Catalytic Transformations of ortho-Alkynylnaphthols

Tetrahedron, Год журнала: 2025, Номер unknown, С. 134726 - 134726

Опубликована: Май 1, 2025

Язык: Английский

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Pd(II)-Catalyzed Tandem Cycloannulative-Alkenylation of o-Alkynyl-Phenols/Anilines with (E)-β-Iodovinyl Sulfones: A Direct Strategy To Construct 3-(Vinyl sulfonyl)benzoheterole Derivatives

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(13), С. 8889 - 8903

Опубликована: Июнь 7, 2023

Benzoheteroles and vinyl sulfones are the most promising pharmaceutical relevance motifs, yet hybrid analogues of these scaffolds still need to be explored. We report herein a general highly efficient Pd(OAc)2-catalyzed intramolecular cyclization vinylation o-alkynylphenols/o-alkynylanilines with (E)-β-iodovinyl under mild reaction conditions. A direct C(sp2)–C(sp2) cross-coupling is enabled for diversity-oriented synthesis sulfone-tethered benzofurans indoles in good high yields excellent stereoselectivity. Notably, this tandem process was consistent at gram scale, situ, generation 2-(phenylethynyl)phenol has also been utilized scalable synthesis. Late-stage synthetic transformations were further explored, including isomerization desulfonylative-sulfenylation. Moreover, several control experiments accomplished, we proposed plausible mechanism based on existing experimental results.

Язык: Английский

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Synthesis of (E)‐β‐Iodovinyl Sulfones via HI‐mediated Vicinal Iodosulfonylation of Alkynes with Sodium Sulfinates

Asian Journal of Organic Chemistry, Год журнала: 2024, Номер 13(6)

Опубликована: Март 21, 2024

Abstract Hydroiodic acid‐mediated vicinal iodosulfonylation reaction of alkynes with sodium sulfinates is proposed for the synthesis ( E )‐ β ‐iodovinyl sulfones. The method easy to operate, environmentally friendly, using inexpensive and easily available raw materials, giving target products good regio‐ stereoselectivity in satisfactory yields.

Язык: Английский

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Trace water in a BF₃·OEt₂ system: a facile access to sulfinyl alkenylsulfones from alkynes and sodium sulfinates

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(38), С. 7776 - 7781

Опубликована: Янв. 1, 2023

An efficient and operationally simple synthesis of β-sulfinyl alkenylsulfones through a BF 3 ·OEt 2 -promoted reaction alkynes sodium sulfinates is developed.

Язык: Английский

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Manganese(iii) acetate in organic synthesis: a review of the past decade

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(23), С. 6850 - 6917

Опубликована: Янв. 1, 2024

In this review, we summarize the latest developments and applications of Mn(OAc) 3 in organic synthesis over past decade, focusing on efforts to achieve milder reaction conditions while expanding scope possibilities.

Язык: Английский

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