Organophotocatalytic Reduction of Benzenes to Cyclohexenes DOI

K. Uma Devi,

Asad Shehzad, Mario P. Wiesenfeldt

и другие.

Journal of the American Chemical Society, Год журнала: 2024, Номер unknown

Опубликована: Дек. 4, 2024

The reduction of abundant benzene rings to scarce C(sp3)-rich motifs is invaluable for drug design, as C(sp3) content known correlate with clinical success. Cyclohexenes are attractive targets, they can be rapidly elaborated into large product libraries and stable against rearomatization. However, partial reactions benzenes cyclohexenes rare have a very narrow scope. Herein we report broadly applicable method that converts electron-poor tolerates Lewis-basic functional groups such triazoles thioethers well reducible cyanides, alkynes, sulfones. reaction utilizes an organic donor induces mild arene by preassociation photoexcitable electron donor–acceptor (EDA) complex isomerization redox-inert 1,4-cyclohexadienes 1,3-cyclohexadienes without strong base in its oxidized thioquinone methide form.

Язык: Английский

Enantioselective Reduction of 1-Naphthamides by Electrochemical Reduction and Catalytic Asymmetric Hydrogenation in Tandem DOI

Xin-Yi Yang,

Xuan-Ge Zhang,

Qi‐Lin Zhou

и другие.

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

Опубликована: Март 13, 2025

Chiral 1-tetrahydronaphthamides are the core structures of many bioactive molecules, yet their efficient asymmetric synthesis from a simple feedstock remains challenge. Herein, we present one-pot strategy that combines electrochemical reduction and ruthenium-catalyzed hydrogenation to achieve enantioselective 1-naphthalenamides chiral 1-tetrahydronaphthamides. The protocol provides practical platform for selectively constructing high-value tetrahydronaphthenes readily available naphthalene feedstock, thereby expanding scope hydrogenation. synthetic utility this is further demonstrated through molecules.

Язык: Английский

Процитировано

0

Skeletal Reorganization of Saturated Six-Membered Aza-cycles to Sulfonated Pyrrolidines under Redox-Neutral Conditions DOI
Shi‐Hui Shi,

Qing-Gen Wang,

Yihan Yang

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 21, 2025

Ring contraction in skeletal reorganization strategies is one of the most intriguing yet surprisingly challenging transformations. Herein, we report for first time a ring tandem sulfonation between saturated six-membered N-heterocyclic nitroxides and sulfonyl hydrazides to access sulfonated pyrrolidine derivatives by an electrochemical redox cascade under redox-neutral metal-free conditions, which unavailable via conventional synthetic approaches. This benign approach has been further demonstrated gram-scale preparation pharmaceutical molecule synthesis mild conditions.

Язык: Английский

Процитировано

0

Highly selective 1,4-hydrogenation of conjugated dienes by photoinduced electron transfer and proton transfer DOI Creative Commons
Changhao Feng, Jiahong Wang, Hao Guo

и другие.

Cell Reports Physical Science, Год журнала: 2025, Номер unknown, С. 102561 - 102561

Опубликована: Апрель 1, 2025

Язык: Английский

Процитировано

0

Steering the selectivity in electrocatalytic hydrogenation of 5-hydroxymethylfurfural via buffer effect DOI

Zhenyu Bao,

Chen Wang, Zhengyu Wang

и другие.

Chemical Engineering Journal, Год журнала: 2025, Номер unknown, С. 163570 - 163570

Опубликована: Май 1, 2025

Язык: Английский

Процитировано

0

Organophotocatalytic Reduction of Benzenes to Cyclohexenes DOI

K. Uma Devi,

Asad Shehzad, Mario P. Wiesenfeldt

и другие.

Journal of the American Chemical Society, Год журнала: 2024, Номер unknown

Опубликована: Дек. 4, 2024

The reduction of abundant benzene rings to scarce C(sp3)-rich motifs is invaluable for drug design, as C(sp3) content known correlate with clinical success. Cyclohexenes are attractive targets, they can be rapidly elaborated into large product libraries and stable against rearomatization. However, partial reactions benzenes cyclohexenes rare have a very narrow scope. Herein we report broadly applicable method that converts electron-poor tolerates Lewis-basic functional groups such triazoles thioethers well reducible cyanides, alkynes, sulfones. reaction utilizes an organic donor induces mild arene by preassociation photoexcitable electron donor–acceptor (EDA) complex isomerization redox-inert 1,4-cyclohexadienes 1,3-cyclohexadienes without strong base in its oxidized thioquinone methide form.

Язык: Английский

Процитировано

1