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

Electric‐Field Catalysis on Carbon Nanotubes in Electromicrofluidic Reactors: Monoterpene Cyclizations DOI Creative Commons
Augustina Jozeliu̅naitė, Shen‐Yi Guo, Naomi Sakai

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 10, 2024

The control over the movement of electrons during chemical reactions with oriented external electric fields (OEEFs) has been predicted to offer a general approach catalysis. Recently, we suggested that many problems realize electric-field catalysis in practice under scalable bulk conditions could possibly be solved on multiwalled carbon nanotubes electromicrofluidic reactors. Here, selected monoterpene cyclizations assess scope our system organic synthesis. We report can function by stabilizing both anionic and cationic transition states, depending orientation applied field. Moreover, promote which are barely accessible Brønsted Lewis acids field-free anion-π cation-π interactions, drive chemoselectivity toward intrinsically disfavored products without need for pyrene interfacers attached substrate prolong binding nanotubes. Finally, interfacing chiral organocatalysts is explored evidence against contributions from redox chemistry provided.

Language: Английский

Citations

0
Electric‐Field Catalysis on Carbon Nanotubes in Electromicrofluidic Reactors: Monoterpene Cyclizations DOI Creative Commons
Augustina Jozeliu̅naitė, Shen‐Yi Guo, Naomi Sakai

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 10, 2024

Abstract The control over the movement of electrons during chemical reactions with oriented external electric fields (OEEFs) has been predicted to offer a general approach catalysis. Recently, we suggested that many problems realize electric‐field catalysis in practice under scalable bulk conditions could possibly be solved on multiwalled carbon nanotubes electromicrofluidic reactors. Here, selected monoterpene cyclizations assess scope our system organic synthesis. We report can function by stabilizing both anionic and cationic transition states, depending orientation applied field. Moreover, promote which are barely accessible Brønsted Lewis acids field‐free anion‐π cation‐π interactions, drive chemoselectivity toward intrinsically disfavored products without need for pyrene interfacers attached substrate prolong binding nanotubes. Finally, interfacing chiral organocatalysts is explored evidence against contributions from redox chemistry provided.

Language: Английский

Citations

0
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