Copper-Catalyzed Deoxygenative C–N Coupling of Epoxides and Sulfonamides DOI
Amitava Hazra,

Sudipta Baur,

Joydev K. Laha

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 28, 2025

An effective approach for the synthesis of N-vinylaromatic sulfonamides using copper-catalyzed deoxygenative cross-coupling epoxides and has been reported. This method allows easy a number N-vinylsulfonamides under mild reaction conditions. protocol is notable its utilization an affordable easy-to-handle wide range N-substituted sulfonamides, cheap readily available copper catalysts, robust functional group tolerance, good to excellent yields. The developed was also applied large-scale syntheses.

Language: Английский

A General Three-Component Nozaki–Hiyama–Kishi-Type Reaction Enabled by Delayed Radical-Polar Crossover DOI
Yanbo Li, Minghao Xu,

Leopold A. Kellermann

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 8, 2025

Nozaki–Hiyama–Kishi (NHK) reactions offer a mild approach for the formation of alcohol motifs through radical-polar crossover-based pathways from various radical precursors. However, application multicomponent NHK-type reactions, which allow multiple bonds in single step, has been largely restricted to bulky alkyl precursors, thus limiting their expanded utilization. Herein, we disclose general three-component reaction enabled by delayed crossover, efficiently tolerates plethora precursors that were previously unavailable. This method enables modular assembly versatile homoallylic alcohols feedstock chemicals with excellent chemo-, regio-, diastereo-, and enantioselectivities step. Experimental studies density functional theory (DFT) calculations reveal kinetically favored an allylchromium(III) species is paramount enforcing crossover over direct addition. Finally, straightforward transformations applications products demonstrated, showcasing synthetic utility this method.

Language: Английский

Citations

1
Merging Photoexcited Nitroarenes with Lewis Acid Catalysis for the Anti-Markovnikov Oxidation of Alkenes DOI Creative Commons
Joshua Paolillo, Mahmoud R. Saleh,

Ethan Junk

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 20, 2025

Herein we describe the oxidation of alkenes to carbonyls and acetonides via interplay photoexcited nitroarenes Lewis acid catalysis. A wide range were oxidized aldehyde ketone products with anti-Markovnikov selectivity when acetone was employed as a co-solvent. Mechanistic studies support that coordination 1,3,2-dioxazolidine intermediate results in 1,2-shift generate carbonyl derivatives nucleophilic substitution pathway for formation acetonides.

Language: Английский

Citations

0
Stereoselective Total Synthesis of Nimbolide DOI
David B. Ryffel,

Peter C. Ryffel,

M. Martinelli

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: April 21, 2025

A stereoselective total synthesis of nimbolide has been achieved in a convergent, 11-step sequence from α-methyl-(R)-carvone. The strategy relied on palladium-catalyzed borylative Heck cyclization where the A-ring core was constructed while simultaneously performing oxidation at C(28). Selective manipulations delivered fully decorated decalin moiety large scale. Then, stereoretentive etherification reaction brought together two fragments and forged critical C-O bond with high selectivity. Finally, regioselective radical late-stage lactonization completed nimbolide.

Language: Английский

Citations

0
Copper-Catalyzed Deoxygenative C–N Coupling of Epoxides and Sulfonamides DOI
Amitava Hazra,

Sudipta Baur,

Joydev K. Laha

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 28, 2025

An effective approach for the synthesis of N-vinylaromatic sulfonamides using copper-catalyzed deoxygenative cross-coupling epoxides and has been reported. This method allows easy a number N-vinylsulfonamides under mild reaction conditions. protocol is notable its utilization an affordable easy-to-handle wide range N-substituted sulfonamides, cheap readily available copper catalysts, robust functional group tolerance, good to excellent yields. The developed was also applied large-scale syntheses.

Language: Английский

Citations

0