Ligand-free copper-catalyzed C(sp<sup>3</sup>)–H imidation of aromatic and aliphatic methyl sulfides with <i>N</i>-fluorobenzenesulfonimide

The AuI complex [Au{N(F)SO2Ph}(SPhos)] (SPhos=dicyclohexyl(2′,6′‐dimethoxy[1,1′‐biphenyl]‐2‐yl)phosphane) (2) bearing a fluoroamido ligand has been synthesized by reaction of the fluorido complex [Au(F)(SPhos)] (1) with NFSI (NFSI=N‐fluorobenzenesulfonimide). A reaction with CO resulted in an unprecedented insertion into the N−F bond at 2. With the carbene precursor N2CH(CO2Et) N−F bond cleavage gave the Au−F bond insertion product [Au{CHF(CO2C2H5)}(SPhos)] (7). The presence of CNtBu led to Au−N cleavage at 2 and concomitant amide formation to give the cationic complex [Au(CNtBu)(SPhos)][N(F)SO2Ph)] (5), which reacted further to give FtBu as well as the cyanido complex [Au(CN)(SPhos)] (6). These results led to the development of a process for the amination of electrophilic organic substrates by transfer of the fluoroamido group NF(SO2Ph)−.

show abstract

Conversion of a Au^I Fluorido Complex into an N‐Fluoroamido Derivative: N−F versus Au−N Reactivity

Rachor

Ahrens

Braun

2022

Angewandte Chemie

View full text Add to dashboard Cite

show abstract

Conversion of a Au^I Fluorido Complex into an N‐Fluoroamido Derivative: N−F versus Au−N Reactivity

2022

View full text Add to dashboard Cite

The Au I complex [Au{N(F)SO 2 Ph}(SPhos)] (SPhos = dicyclohexyl(2',6'-dimethoxy[1,1'-biphenyl]-2yl)phosphane) (2) bearing a fluoroamido ligand has been synthesized by reaction of the fluorido complex [Au(F)(SPhos)] (1) with NFSI (NFSI = N-fluorobenzenesulfonimide). A reaction with CO resulted in an unprecedented insertion into the NÀ F bond at 2. With the carbene precursor N 2 CH(CO 2 Et) NÀ F bond cleavage gave the AuÀ F bond insertion product [Au{CHF-(CO 2 C 2 H 5 )}(SPhos)] (7). The presence of CNtBu led to AuÀ N cleavage at 2 and concomitant amide formation to give the cationic complex [Au(CNtBu)(SPhos)][N-(F)SO 2 Ph)] ( 5), which reacted further to give FtBu as well as the cyanido complex [Au(CN)(SPhos)] ( 6). These results led to the development of a process for the amination of electrophilic organic substrates by transfer of the fluoroamido group NF(SO 2 Ph) À .

show abstract

Recent advances in direct α-C(sp3)-H bond functionalization of thioethers

Tang

Yang

et al. 2022

Green Synthesis and Catalysis

View full text Add to dashboard Cite

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

Ligand-free copper-catalyzed C(sp³)–H imidation of aromatic and aliphatic methyl sulfides with N-fluorobenzenesulfonimide

Abstract: A novel and efficient process for ligand-free C(sp3)–H amination of aromatic and aliphatic methyl sulfides with N-fluorobenzenesulfonimide catalyzed by copper catalysts was developed.

Cited by 6 publications

References 79 publications

Conversion of a Au^I Fluorido Complex into an N‐Fluoroamido Derivative: N−F versus Au−N Reactivity

Conversion of a Au^I Fluorido Complex into an N‐Fluoroamido Derivative: N−F versus Au−N Reactivity

Conversion of a Au^I Fluorido Complex into an N‐Fluoroamido Derivative: N−F versus Au−N Reactivity

Recent advances in direct α-C(sp3)-H bond functionalization of thioethers

Contact Info

Product

Resources

About

Ligand-free copper-catalyzed C(sp3)–H imidation of aromatic and aliphatic methyl sulfides with N-fluorobenzenesulfonimide

Abstract: A novel and efficient process for ligand-free C(sp3)–H amination of aromatic and aliphatic methyl sulfides with N-fluorobenzenesulfonimide catalyzed by copper catalysts was developed.

Cited by 6 publications

References 79 publications

Conversion of a AuI Fluorido Complex into an N‐Fluoroamido Derivative: N−F versus Au−N Reactivity

Conversion of a AuI Fluorido Complex into an N‐Fluoroamido Derivative: N−F versus Au−N Reactivity

Conversion of a AuI Fluorido Complex into an N‐Fluoroamido Derivative: N−F versus Au−N Reactivity

Recent advances in direct α-C(sp3)-H bond functionalization of thioethers

Contact Info

Product

Resources

About

Ligand-free copper-catalyzed C(sp³)–H imidation of aromatic and aliphatic methyl sulfides with N-fluorobenzenesulfonimide

Conversion of a Au^I Fluorido Complex into an N‐Fluoroamido Derivative: N−F versus Au−N Reactivity

Conversion of a Au^I Fluorido Complex into an N‐Fluoroamido Derivative: N−F versus Au−N Reactivity

Conversion of a Au^I Fluorido Complex into an N‐Fluoroamido Derivative: N−F versus Au−N Reactivity