Photo‐Induced Oxyamination of Alkenyl Acids towards Amino Lactones

Pan, Changduo; Chen, Dongdong; Zeng, Miao; Tian, Haoyang; Yu, Jin‐Tao

doi:10.1002/ejoc.202301065

Cited by 3 publications

(1 citation statement)

References 79 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In continuation of our keen interest in exploring radical fluorosulfonylation methodology, − we aimed to design bench-stable and readily available radical reagents to facilitate fluorosulfonamidation reactions. Drawing inspiration from recent advances in the utilization of N-functionalized pyridinium salts as versatile reagents, − we successfully synthesized the required N -fluorosulfamoyl pyridium reagents (NFSAP- 1a ) in two steps from commercially available N -aminopyridium iodide and the structure of 1a was elucidated through X-ray single-crystal diffraction (CCDC: 2353363). We envisioned that N-centered fluorosulfamoyl radicals could be generated through the cleavage of weak N-heteroatom bonds tethered to redox-active scaffolds.…”

Section: Introductionmentioning

confidence: 99%

Direct Fluorosulfonamidation of (Hetero)arenes and Alkenes with Photoredox-Active Fluorosulfamoyl Radical Reagents

Xiong,

Chen,

Zhang

et al. 2024

ACS Catal.

View full text Add to dashboard Cite

Sulfur(VI) fluoride exchange (SuFEx) is a second-generation click chemistry reaction that relies on the unique reactivities of S VI −F bonds. The development of efficient methods for incorporating a S(VI)−F motif into molecules is of great significance. Sulfamoyl fluorides (R 1 R 2 NSO 2 F), serving as versatile SuFExable hubs, are typically synthesized by using " + SO 2 F" reagents to establish N-SO 2 F bonds. In this study, we report the development of N-fluorosulfamoyl pyridium salts (NFSAPs) as radical fluorosulfonamidation reagents that are readily accessible and bench-stable. By employing NFSAPs as essential fluorosulfamoyl radical (•NSO 2 F) precursors, the direct installation of the NSO 2 F group onto (hetero)arenes and alkenes is achieved through distinct C−N bond formation reactions. This platform facilitates the collective synthesis of highly functionalized N-aryl, N-alkyl, and N-alkenyl sulfamoyl fluorides (R 1 R 2 NSO 2 F) under mild photocatalytic conditions and has been applied in the late-stage functionalization of pharmaceuticals and peptides.

show abstract

Section: Introductionmentioning

confidence: 99%

Direct Fluorosulfonamidation of (Hetero)arenes and Alkenes with Photoredox-Active Fluorosulfamoyl Radical Reagents

Xiong,

Chen,

Zhang

et al. 2024

ACS Catal.

View full text Add to dashboard Cite

show abstract

Photocatalyzed Acylmethylation/Cyclization of Unactivated Alkenes with Sulfoxonium Ylides towards Acylmethylated Polycyclic Quinazolinones

Wu,

Liu,

et al. 2024

ChemCatChem

View full text Add to dashboard Cite

The synthesis of acylmethylatated pyrrolo‐quinazolinones was developed via photo‐induced cascade radical addition/cyclization of N‐(but‐3‐enyl)quinazolin‐4(3H)‐ones with sulfoxonium ylides using 4CzIPN as the photocatalyst. This approach was also suitable for the construction of acylmethylatated piperidino‐quinazolinones. This protocol features with mild conditions, convenient operation, broad substrate scope and good functional group compatibility.

show abstract

Electrochemical Oxidative Cascade Cyclization of Alkenyl Alcohols with External Nucleophiles to Access Amino- and Hydroxy-Functionalized O-Heterocycles

Ren,

Wang,

Zha

et al. 2024

J. Org. Chem.

View full text Add to dashboard Cite

A convenient electrochemical oxidative cascade cyclization of alkenes equipped with pendant alcohols with general nucleophiles was developed. Using readily available diarylmethanimine and carboxylic acids as nucleophilic sources, a broad range of internal alkene and terminal alkene substrates could produce RCO 2 -and Ar 2 CN-functionalized O-heterocycles in moderate to high yields without the requirement for external oxidants and metals. These resulting products can subsequently be hydrolyzed to yield valuable NH 2 -and OH-functionalized tetrahydrofurans and tetrahydropyranes under mild conditions. Importantly, the efficient conversion of secondary alcohol products to amines with complete inversion of configuration enhances the methodology, enabling the construction of 2-aryl-3-amino tetrahydrofuran with high and complementary diastereoselectivity.

show abstract

Photo‐Induced Oxyamination of Alkenyl Acids towards Amino Lactones

Cited by 3 publications

References 79 publications

Direct Fluorosulfonamidation of (Hetero)arenes and Alkenes with Photoredox-Active Fluorosulfamoyl Radical Reagents

Direct Fluorosulfonamidation of (Hetero)arenes and Alkenes with Photoredox-Active Fluorosulfamoyl Radical Reagents

Photocatalyzed Acylmethylation/Cyclization of Unactivated Alkenes with Sulfoxonium Ylides towards Acylmethylated Polycyclic Quinazolinones

Electrochemical Oxidative Cascade Cyclization of Alkenyl Alcohols with External Nucleophiles to Access Amino- and Hydroxy-Functionalized O-Heterocycles

Contact Info

Product

Resources

About