Electrochemical α-C(sp3)–H/N–H Cross-Coupling of Isochromans and Azoles DOI Creative Commons
Guoping Li, Bing Yan, Liangliang Wu

et al.

Molecules, Journal Year: 2024, Volume and Issue: 30(1), P. 4 - 4

Published: Dec. 24, 2024

Isochroman and azole moieties are both present in a wide variety of biologically active molecules. Their efficient combination under mild reaction conditions is beneficial for obtaining small-molecule drug candidates. In this paper, we describe electrochemical α-C(sp3)–H/N–H cross-coupling reactions between isochromans azoles, yielding products moderate to excellent yields. This protocol does not require any catalysts or exogenous oxidants can be performed at room temperature air. Control experiments cyclic voltammetry showed that the may proceed through radical coupling nucleophilic addition processes.

Language: Английский

A Voltage-Controlled Strategy for Modular Shono-Type Amination DOI
Siyuan Su, Yahui Guo, Bryan Parnitzke

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(42), P. 28663 - 28668

Published: Oct. 14, 2024

Shono-type oxidation to generate functionalized heterocycles is a powerful method for late-stage diversification of relevant pharmacophores; however, development beyond oxygen-based nucleophiles remains underdeveloped. The limited scope can often be ascribed constant current electrolysis resulting in potential drifts that oxidize desired nucleophilic partner. Herein, we report voltage-controlled strategy selectively broad substrates, enabling modular C-N bond formation from protected amine nucleophiles. We implement an electroanalytically guided workflow using cyclic voltammetry (CV) and differential pulse (DPV) identify potentials across range heterocyclic substrates. Controlled (CPE) generates α-functionalized products moderate good yields carbamate-, sulfonamide-, benzamide-derived importance voltage control further exemplified through systematic study comparing our developed CPE (CCE) protocols. Voltage-guided CCE traditionally optimized reveal the maintaining high selectivity over scope; case with morpholine-derived substrate illustrates negative impact drifting under CCE. Sulfonamide drugs, which have significant overlap model are rendered competent CPE. Lastly, sequential C-O functionalization difunctionalized pyrrolidines broadening utility this reaction.

Language: Английский

Citations

4
Regioselective, Lewis Acid-Catalyzed Ring-Openings of 2,3-Aziridyl Alcohols with Azoles DOI
Bin Zheng, Mark S. Taylor

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

Published: April 25, 2025

Methods for regioselective ring-opening reactions of N-sulfonyl-protected aziridyl alcohols with azole nucleophiles have been developed. Several classes azoles, including indazole, substituted pyrazole, benzotriazole, and tetrazole, employed as reaction partners, giving rise to C3-selective opening >3:1 N-selectivity. BF3•OEt2 is the optimal catalyst most substrate combinations, although examples where diphenylborinic acid (Ph2BOH) provides higher yields, or proceed efficiently without a catalyst, are also described. Computational modeling BF3•OEt2-catalyzed consistent observed regiochemical outcome. The calculated transition state appears be stabilized by an unconventional OH···FB hydrogen-bonding interaction.

Language: Английский

Citations

0
Direct Decarboxylative C−N Coupling with Dioxazolones Mediated by a Base DOI

Bai-Hua Niu,

Xi‐Rui Xia,

Ran Lu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

By reacting carboxylic acids with dioxazolones in the presence of a base, wide variety amides, particularly acylated chiral amines, can be synthesized through decarboxylative amidation.

Language: Английский

Citations

1
Electrochemical α-C(sp3)–H/N–H Cross-Coupling of Isochromans and Azoles DOI Creative Commons
Guoping Li, Bing Yan, Liangliang Wu

et al.

Molecules, Journal Year: 2024, Volume and Issue: 30(1), P. 4 - 4

Published: Dec. 24, 2024

Isochroman and azole moieties are both present in a wide variety of biologically active molecules. Their efficient combination under mild reaction conditions is beneficial for obtaining small-molecule drug candidates. In this paper, we describe electrochemical α-C(sp3)–H/N–H cross-coupling reactions between isochromans azoles, yielding products moderate to excellent yields. This protocol does not require any catalysts or exogenous oxidants can be performed at room temperature air. Control experiments cyclic voltammetry showed that the may proceed through radical coupling nucleophilic addition processes.

Language: Английский

Citations

0