Organophotocatalytic Reduction of Benzenes to Cyclohexenes DOI

K. Uma Devi,

Asad Shehzad, Mario P. Wiesenfeldt

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 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.

Language: 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

et al.

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

Published: March 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.

Language: Английский

Citations

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

et al.

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

Published: March 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.

Language: Английский

Citations

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

et al.

Cell Reports Physical Science, Journal Year: 2025, Volume and Issue: unknown, P. 102561 - 102561

Published: April 1, 2025

Language: Английский

Citations

0
Organophotocatalytic Reduction of Benzenes to Cyclohexenes DOI

K. Uma Devi,

Asad Shehzad, Mario P. Wiesenfeldt

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 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.

Language: Английский

Citations

1