Alkoxy Radical‐Triggered 1,1,2‐Trifunctionalization of Unactivated Alkenes towards N,O‐Spiroaminals DOI
Min Dong, Xi Lu, Yu Sha

et al.

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 18, 2025

Comprehensive Summary N,O‐Spiroaminals have potential biological activities and abilities to modulate the physicochemical pharmacokinetic properties of drug molecules. However, effective catalytic methods for efficient construction N,O‐spiroaminals are still limited date. Herein, we report a novel 1,1,2‐trifunctionalization unactivated alkenes rapidly efficiently obtain diverse array architecturally intriguing N,O‐spiroaminals. This methodology exhibits broad substrate scope, good functional group compatibility, synthetic utility by scale‐up reaction, product derivatizations late‐stage functionalization complex biorelevant molecule. Notably, this transformation selectively allows formation three new chemical bonds (C–O, C–C, C–N) one spiro quaternary carbon center across C‐C double bonds.

Language: Английский

Photocatalytic Three-Component Reductive Coupling Synthesis of gem-Difluorohomoallyl Secondary Amines DOI

Bingbing Feng,

Meifang Tang,

Rui Xiao

et al.

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

Published: Jan. 23, 2025

gem-Difluorohomoallyl amines, an important class of gem-difluoroalkenes, are prevalent moieties in many bioactive compounds. However, limited methods suitable for the synthesis this type compound containing secondary amines. Here, we display a photocatalytic multicomponent protocol gem-difluoroalkenes which makes use readily available materials: arylamines, alkyl aldehydes, and α-trifluoromethyl alkenes. Moreover, ketones amines also substrates. Preliminary mechanistic experiments indicate that key α-amino radical was involved, generated from reduction situ-formed imines (or iminium ions) by reduced photocatalyst. Subsequent addition to alkenes β-F elimination deliver desired products.

Language: Английский

Citations

4
Decatungstate-Catalyzed Hydrosilylation of α-Trifluoromethylalkenes for Construction of α-Trifluoromethyl-β-silanes DOI
M. Xiao,

Yidong Lang,

Ziqiang Cheng

et al.

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

Published: April 18, 2025

The hydrosilylation of alkenes is a pivotal transformation for the synthesis organosilanes; however, fluorine-containing limited due to facile β-fluoride elimination. Herein, by employing direct hydrogen atom transfer (HAT) catalyst, tetrabutylammonium decatungstate (TBADT), and using disulfide as co-catalyst, we have successfully developed mild photocatalytic α-trifluoromethylalkenes α-trifluoromethyl-β-silanes. Our method features conditions, good regioselectivity, compatibility. elimination was fully inhibited. A radical mechanism proposed based on preliminary results.

Language: Английский

Citations

2
Visible-Light-Induced C–H Alkylation of 1,2,4-Triazine-3,5(2H,4H)-diones via Infrequent 1,2-Hydrogen-Atom Transfer DOI
Mi Wang, Yangyang Wang, Jie Wang

et al.

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

Published: May 19, 2025

1,2,4-Triazine-3,5(2H,4H)-diones are widely present in various drug molecules and bioactive molecules. A visible-light-driven C-H alkylation of 1,2,4-triazine-3,5(2H,4H)-diones via 1,2-hydrogen-atom transfer (1,2-HAT) amide radicals is first reported, providing an environmentally friendly sustainable pathway to enrich the structural functional diversity 1,2,4-triazine-3,5(2H,4H)-diones. This novel protocol characterized by mild metal-free reaction conditions, operationally simple method, good group tolerance. To our delight, other heterocycles, such as isoquinoline coumarin, also undergo reactions construct C(sp2)-C(sp3) bonds infrequent 1,2-HAT under current conditions.

Language: Английский

Citations

0
Photoexcited Copper-Catalyzed Difunctionalization of Alkenes for the Synthesis of 2,5-Diamino Acid Derivatives via Uncommon 1,2-Hydrogen Atom Transfer of Amidyl Radicals DOI
Xue Zhang,

Liulin Jiao,

Ting Yuan

et al.

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

Published: May 25, 2025

Compared with 1,5-hydrogen atom transfer (1,5-HAT) processes, 1,2-HAT processes have been reported less frequently. And, the synthesis of 2,5-diamino acid derivatives via a mild photocatalytic approach has not yet. Herein, we report photoexcited copper-catalyzed difunctionalization alkenes for uncommon 1,2-HAT. The potential synthetic merit this reaction is proven through scale-up reaction. Notably, new protocol successfully applied to obtain series derivatives.

Language: Английский

Citations

0
Alkoxy Radical‐Triggered 1,1,2‐Trifunctionalization of Unactivated Alkenes towards N,O‐Spiroaminals DOI
Min Dong, Xi Lu, Yu Sha

et al.

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 18, 2025

Comprehensive Summary N,O‐Spiroaminals have potential biological activities and abilities to modulate the physicochemical pharmacokinetic properties of drug molecules. However, effective catalytic methods for efficient construction N,O‐spiroaminals are still limited date. Herein, we report a novel 1,1,2‐trifunctionalization unactivated alkenes rapidly efficiently obtain diverse array architecturally intriguing N,O‐spiroaminals. This methodology exhibits broad substrate scope, good functional group compatibility, synthetic utility by scale‐up reaction, product derivatizations late‐stage functionalization complex biorelevant molecule. Notably, this transformation selectively allows formation three new chemical bonds (C–O, C–C, C–N) one spiro quaternary carbon center across C‐C double bonds.

Language: Английский

Citations

0