Remote Migratory Reductive Arylation of Unactivated Alkenes Enabled by Electrochemical Nickel Catalysis DOI Creative Commons
Chao Xu,

A. Ruhan,

Xiao‐Feng Wu

et al.

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

Published: Oct. 29, 2024

Transition metal-catalyzed cross-coupling reaction between organometallic reagents and electrophiles is a potent method for constructing C(sp

Language: Английский

The Strategies towards Electrochemical Generation of Aryl Radicals DOI
Xiaobao Zeng

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: unknown

Published: July 16, 2024

The advancement in electrochemical techniques has unlocked a new path for achieving unprecedented oxidations and reductions of aryl radical precursors controlled selective manner. This approach facilitates the construction aromatic carbon-carbon carbon-heteroatom bonds. In light green merits growing importance this technique chemistry, review aims to provide an overview recent advance generation radicals organized by precursor type, with focus on substrate scope, limitation, underlying mechanism, thereby inspiring future work generation.

Language: Английский

Citations

11

Electron Donor–Acceptor Complex Enabled Cyclization/Sulfonylation Cascade of N-Heterocycles with Thianthrenium Salts DOI

Zhengjun He,

Zhi Li,

Shuo Lai

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(31), P. 6652 - 6657

Published: July 26, 2024

We report a visible-light-promoted cyclization/sulfonylation cascade of N-heterocycles with thianthrenium salts using DABSO as the SO2 surrogate. This method features excellent functional group tolerance, wide substrate scope, and late-stage elaboration bioactive relevant molecules. Mechanistic investigations reveal that photoactive electron donor–acceptor (EDA) complexes between DABCO are capable generation aryl radicals, which induce following insertion by attacking DABSO, thus triggering key radical cyclization step.

Language: Английский

Citations

10

Hydrodeuteroalkylation of Unactivated Olefins Using Thianthrenium Salts DOI
Jie Zhang,

Mengjie Jiao,

Zheng Lu

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(36)

Published: June 13, 2024

Isotopically labeled alkanes play a crucial role in organic and pharmaceutical chemistry. While some deuterated methylating agents are readily available, the limited accessibility of other deuteroalkyl reagents has hindered synthesis corresponding products. In this study, we introduce nickel-catalyzed system that facilitates various deuterium-labeled through hydrodeuteroalkylation d2-labeled alkyl TT salts with unactivated alkenes. Diverging from traditional reagents, thianthrenium (TT) can effectively selectively deuterium at α position chains using D

Language: Английский

Citations

8

Parametrization of κ2-N,O-Oxazoline Preligands for Enantioselective Cobaltaelectro-Catalyzed C–H Activations DOI Creative Commons
Suman Dana, Neeraj Kumar Pandit, Philipp Boos

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 4450 - 4459

Published: Feb. 28, 2025

Enantioselective electrocatalyzed C–H activations have emerged as a transformative platform for the assembly of value-added chiral organic molecules. Despite recent progress, construction multiple C(sp3)-stereogenic centers via C(sp3)–C(sp3) bond formation has thus far proven to be elusive. In contrast, we herein report an annulative activation strategy, generating Fsp3-rich molecules with high levels diastereo- and enantioselectivity. κ2-N,O-oxazoline preligands were effectively employed in enantioselective cobalt(III)-catalyzed reactions. Using DFT-derived descriptors regression statistical modeling, performed parametrization study on modularity preligands. The resulted model describing ligands' selectivity characterized by key steric, electronic, interaction behaviors.

Language: Английский

Citations

1

Electrochemical Cyclization of o-Aminyl Azobenzenes: Roles of Aldehydes in N–N Bond Cleavage DOI
Anni Li,

Anna Gao,

K. K. N. CHEN

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(30), P. 6324 - 6329

Published: July 22, 2024

Direct functionalization of azobenzenes provides an approach to obtaining valuable molecules in synthetic chemistry. However, efficient method for the cleavage N═N bond azobenzenes, which is a key process this transformation, still lacking. We herein disclose electrochemical reduction-induced cyclization with aldehydes via cleavage. This proceeds well absence any transition metals or external chemical oxidants, leading formation N-protected benzimidazoles moderate good yields.

Language: Английский

Citations

4

A Catalyst- and Thiol-Free Protocol for Arene C–H Thioetherification via Photoactive Electron Donor–Acceptor Complexes DOI
Ang Gao,

Hongqiong Liu,

Yanan Zhou

et al.

Green Chemistry, Journal Year: 2025, Volume and Issue: 27(8), P. 2286 - 2292

Published: Jan. 1, 2025

We present a catalyst- and thiol-free protocol for arene C–H thioetherification under visible light irradiation.

Language: Английский

Citations

0

Electrochemical Preparation and Transformation of Sulfonium Salts DOI Creative Commons
Takuya Michiyuki, Lutz Ackermann

ChemElectroChem, Journal Year: 2025, Volume and Issue: unknown

Published: March 5, 2025

Abstract Sulfonium salts are typically bench‐stable and readily available reagents that showcase diverse chemical reactivities. Owing to these synthetically valuable features, sulfonium salt chemistry has witnessed considerable momentum over the past decades. Particularly, merger of electrosynthesis enabled utilization electric current in place cost‐intensive hazardous redox agents maximize attractive characteristics salts. Additionally, electrochemistry allowed chemists dial desired potential, offering selective access target products otherwise unattainable by either thermal or photochemical manifolds. These advantages led major advances chemistry. Thus, we, herein, provide an overview early pioneering findings recent progress devoted organic associated with until December 2024, aiming stimulate future this rapidly evolving arena.

Language: Английский

Citations

0

Electrochemical N‐Centered Radical‐Triggered Intramolecular N‐N Coupling for the Cyclization of o‐Aminyl Azobenzenes DOI Open Access

Anna Gao,

K. K. N. CHEN,

Fang Ma

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(46)

Published: Aug. 28, 2024

Abstract An electrochemical radical cyclization of o ‐aminyl azobenzenes via N ‐centered generation has been developed for the synthesis benzotriazoles. The bearing a sulfonyl protection on amine readily proceeds in absence any external transition metal catalyst or chemical oxidant, and exhibits good tolerance towards functional groups.

Language: Английский

Citations

1

Hydrodeuteroalkylation of Unactivated Olefins Using Thianthrenium Salts DOI
Jie Zhang,

Meng-Jie Jiao,

Zheng Lu

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(36)

Published: June 13, 2024

Abstract Isotopically labeled alkanes play a crucial role in organic and pharmaceutical chemistry. While some deuterated methylating agents are readily available, the limited accessibility of other deuteroalkyl reagents has hindered synthesis corresponding products. In this study, we introduce nickel‐catalyzed system that facilitates various deuterium‐labeled through hydrodeuteroalkylation d2‐labeled alkyl TT salts with unactivated alkenes. Diverging from traditional reagents, thianthrenium (TT) can effectively selectively deuterium at α position chains using D 2 O as source via single‐step pH‐dependent hydrogen isotope exchange (HIE). Our method allows for high incorporation, offers precise control over site insertion within an chain. This technique proves to be invaluable compounds, especially those relevance.

Language: Английский

Citations

0

Efficient Accessibility of Indole and Pyrrole Nuclei via Late-Stage Aryl C-H Activation of Drug Molecules Promoted by Thianthrenium Salts DOI

Wangcheng Hu,

Tingting Yang, Shuguang Chen

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

An efficient redox-neutral palladium-catalyzed system has been developed to introduce indole and pyrrole various bioactive molecules via late-stage aryl C–H activation, providing a robust tool explore structure–activity relationships (SARs).

Language: Английский

Citations

0