Electricity‐Driven Strain‐Release Cascade Cyclization of Bicyclo[1.1.0]butane (BCB): Stereoselective Synthesis of Functionalized Spirocyclobutyl Oxindoles DOI
Rajib Maity, Satya Paul, Ankita Sen

et al.

ChemSusChem, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 23, 2024

Abstract Spirocyclobutyl oxindoles, characterized by their unique three‐dimensional structures, are valuable building blocks for many pharmacophores and drug units. However, stereoselective synthetic strategies these scaffolds remain underdeveloped, with most existing methods relying on transition metal catalysts stoichiometric redox reagents. In this work, we introduce an electrochemical strain‐release driven cascade spirocyclization of bicyclo[1.1.0]butane (BCB) derivatives the synthesis functionalized spirocyclobutyl oxindoles. Tetrabutylammonium bromide serves a dual purpose as both supporting electrolyte brominating agent. The method offers broad substrate scope, high atom economy, excellent diastereoselectivity. stereoselectivity product is controlled minimizing dipolar repulsion between amide C=O C−Br bonds. We also explored methodology′s versatility applying it to various functionalizations demonstrated its scalability practical use. efficient derivatization products allowed rapid creation diverse library

Language: Английский

Electrochemical Synthesis of Vinyl Sulfonates Mediated by Bromine Radicals DOI
Yong Huang, Yuyuan Zhang, Yujing Zhou

et al.

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

Published: March 10, 2025

Vinyl sulfonates are vital intermediates in organic synthesis, serving as versatile electrophiles various cross-coupling reactions. Despite their significance, direct methods for synthesizing vinyl from styrenes have been limited. In this study, we introduce an innovative electrochemical approach that leverages bromine radical mediation to facilitate the synthesis of sulfonates, cheap nBu4NBr acts both electrolyte and a catalytic amount. This process involves reaction with sodium sulfinates water under conditions, offering straightforward pathway these compounds. The developed strategy is characterized by its high efficiency, operational simplicity, environmentally benign nature, adhering principles green chemistry while ensuring atom economy remarkable regioselectivity. Furthermore, methodology proves effective gram-scale allows subsequent functionalization sulfonate products pharmaceutical derivatives, thus broadening potential applications techniques styrene functionalization.

Language: Английский

Citations

0
A Metal-Catalyzed Tunable Reaction of Ylides with Hydroxylamine Derivatives DOI
Honglin Song,

N. F. Chen,

Banpeng Cao

et al.

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

Published: March 25, 2025

In this work, a tunable reaction of metal acyl nitrene with ylides is reported for the divergent synthesis enamides and α,α-dicarbonyl phosphorus ylides. The featured mild conditions, good efficiency, broad generality. particular, resulting could be structurally elaborated into potential useful scaffolds. Mechanism investigation suggests that formation was ascribed to nucleophilic substitution ferric sulfur It believed represents an initial example preparing from iron-catalyzed transfer.

Language: Английский

Citations

0
Molecular Insights into Converting Hydroxide Adenosyltransferase into Halogenase DOI
Yixun Jiang, Mingdong Yao, Jianqiang Feng

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: 72(22), P. 12685 - 12695

Published: May 21, 2024

Halogenation plays a unique role in the design of agrochemicals. Enzymatic halogenation reactions have attracted great attention due to their excellent specificity and mild reaction conditions.

Language: Английский

Citations

1
Electrochemical Bromination of Arenes in a 200% Cell DOI Creative Commons
Sara Torabi, Mahdi Jamshidi, Gerhard Hilt

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 25, 2024

Herein, we describe the investigation of electrochemical bromination electron-rich arenes in a 200% cell. For this application, at first, influence an excess supporting electrolyte (Bu

Language: Английский

Citations

0
Electricity‐Driven Strain‐Release Cascade Cyclization of Bicyclo[1.1.0]butane (BCB): Stereoselective Synthesis of Functionalized Spirocyclobutyl Oxindoles DOI
Rajib Maity, Satya Paul, Ankita Sen

et al.

ChemSusChem, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 23, 2024

Abstract Spirocyclobutyl oxindoles, characterized by their unique three‐dimensional structures, are valuable building blocks for many pharmacophores and drug units. However, stereoselective synthetic strategies these scaffolds remain underdeveloped, with most existing methods relying on transition metal catalysts stoichiometric redox reagents. In this work, we introduce an electrochemical strain‐release driven cascade spirocyclization of bicyclo[1.1.0]butane (BCB) derivatives the synthesis functionalized spirocyclobutyl oxindoles. Tetrabutylammonium bromide serves a dual purpose as both supporting electrolyte brominating agent. The method offers broad substrate scope, high atom economy, excellent diastereoselectivity. stereoselectivity product is controlled minimizing dipolar repulsion between amide C=O C−Br bonds. We also explored methodology′s versatility applying it to various functionalizations demonstrated its scalability practical use. efficient derivatization products allowed rapid creation diverse library

Language: Английский

Citations

0