Synthesis of Primary and Secondary Amines via Electrochemical Reduction of Hydrazines DOI

Dong Wang,

Qiulu Wang,

Mingxia Liu

и другие.

Organic Letters, Год журнала: 2024, Номер 26(51), С. 11123 - 11128

Опубликована: Дек. 13, 2024

We herein introduce an electrochemical route for the N–N bond cleavage of hydrazines. This mild and green methodology utilized readily available mono- 1,1-disubstituted hydrazines or their HCl salts as starting materials to access a broad scope primary secondary amines in high yields. The mechanistic investigation suggests that amine product is formed by consecutive SET reduction, utilization hydrazine salt important providing sufficient conductivity acidity facilitate this reaction.

Язык: Английский

Oxa-π, σ-Methane Rearrangement Approach for Epoxide Synthesis DOI

Qiansen Wang,

Yu Zheng,

Wen-Tao Wu

и другие.

Journal of the American Chemical Society, Год журнала: 2025, Номер unknown

Опубликована: Март 30, 2025

Epoxides are significant chemicals that utilized across various fields. Here, we describe an unprecedented photochemical rearrangement approach for synthesizing a diverse collection of epoxides enabled by energy transfer catalysis under visible light conditions. The process enables the easy preparation α-amino-substituted epoxide derivatives with broad substrate scope, functional group tolerance, and mild reaction Furthermore, this photorearrangement has also been applied in complex architectures, could be easily transferred to amino alcohol derivatives. Overall, oxa-π, σ-methane provides complementary strategy existing methods through catalysis.

Язык: Английский

Процитировано

2
Photocatalytic 1,3-Difluoroalkylcarboxylation of Alkenes by Triple Kinetic-Controlled Radical Self-Ordering DOI Creative Commons

Hong Fu,

Zuo-Shuai Wang,

Sijia Li

и другие.

Chemical Science, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

A transition-metal-free protocol for the unsymmetrical radical 1,3-difunctionalization of alkenes has been established first time in form 1,3-difluoroalkylcarboxylation by a photocatalytic three-component reaction allyl formates, trifluoroacetanilides, and cesium formate. This employs formate as carboxylating reagent trifluoroacetanilide difluoroalkylating via C-F bond activation. As result, series previously inaccessible difluorinated adipic acid derivatives can be easily efficient prepared. Mechanism studies reveal that triple kinetic-controlled self-ordering is key to this unique reaction. sorting involves fast initiation CO2 anion its chemoselective addition reduction, followed slow generation fluoroalkyl chemo-/regioselective addition. Notably, strategy also suitable cyclic through diastereoselectively constructing two or three consecutive stereocenters.

Язык: Английский

Процитировано

0
Energy-Transfer-Enabled 1,4-Amino Migration and C–O Diradical Recombination for Norrish–Yang-Type Epoxidation DOI
Danna Chen,

Lulu Qin,

Dan Luo

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Май 22, 2025

An energy-transfer-enabled photochemical strategy merges 1,4-nitrogen migration with Norrish-Yang-type epoxidation to achieve skeletal editing of molecular frameworks. This approach bypasses classical di-π-methane rearrangements, providing an oxidant-free and atom-economical route epoxides via controlled C-O diradical recombination. The protocol accommodates >40 diverse substrates, including arenes, heterocycles, bioactive motifs, enabling late-stage functionalization complex architectures. Scalability is demonstrated through gram-scale synthesis (84% yield) one-pot cascades. Mechanistic studies reveal a triplet energy-transfer pathway distinct from radical chain processes, nitrogen directing regioselective

Язык: Английский

Процитировано

0
Photocatalyzed Imino-Difluoromethylation of Alkenes with Bifunctional Oxime Esters DOI
Zhiwei Chen, Shuhang Yang, Liping Wu

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(18), С. 13585 - 13594

Опубликована: Сен. 11, 2024

Herein, we report a simple and versatile difluoromethylene-imide reaction in which series of olefins can undergo difluoromethylenimine under photocatalytic conditions through an energy transfer (EnT) process. The has mild wide range applicability. We successfully synthesized 27 molecules containing difluoromethylene units, featuring easily accessible starting materials operational simplicity.

Язык: Английский

Процитировано

2
Synthesis of Primary and Secondary Amines via Electrochemical Reduction of Hydrazines DOI

Dong Wang,

Qiulu Wang,

Mingxia Liu

и другие.

Organic Letters, Год журнала: 2024, Номер 26(51), С. 11123 - 11128

Опубликована: Дек. 13, 2024

We herein introduce an electrochemical route for the N–N bond cleavage of hydrazines. This mild and green methodology utilized readily available mono- 1,1-disubstituted hydrazines or their HCl salts as starting materials to access a broad scope primary secondary amines in high yields. The mechanistic investigation suggests that amine product is formed by consecutive SET reduction, utilization hydrazine salt important providing sufficient conductivity acidity facilitate this reaction.

Язык: Английский

Процитировано

2