Photo-induced nickel-mediated cross-electrophile coupling for alkylated allenes via electron donor–acceptor complexes DOI
Zhao‐Zhao Zhou,

Xiaofeng Zhai,

Shuliang Zhang

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 10(2), P. 298 - 303

Published: Nov. 9, 2022

The first photo-induced nickel-mediated regioselective radical–radical cross-electrophile coupling process with alkyl NHP esters and EDA complexes for alkylated allenes is described.

Language: Английский

Dual-Role Halogen-Bonding-Assisted EDA-SET/HAT Photoreaction System with Phenol Catalyst and Aryl Iodide: Visible-Light-Driven Carbon–Carbon Bond Formation DOI
Tatsuhiro Uchikura,

Kazushi Tsubono,

Yurina Hara

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(22), P. 15499 - 15510

Published: Nov. 2, 2022

Electron donor-acceptor (EDA) complex-mediated single-electron transfer (SET) is a crucial method for generating carbon radicals. Hydrogen atom (HAT) enables the direct generation of alkyl We report dual-role EDA-SET/HAT photoreaction system carbon-carbon bond formation using phenol catalyst and aryl iodide. This facilitates addition radicals generated from ethers, amide, sulfide, cycloalkane to arenes. Mechanistic studies revealed that EDA complex mediated by halogen bonding between phenoxide Irradiation with visible light generates an radical, which abstracts hydrogen sp3 form radical.

Language: Английский

Citations

28
Three-Component Aminoheteroarylation of Alkenes via Photoinduced EDA Complex Activation DOI
Chengcheng Shi, Lin Guo, Han Gao

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(42), P. 7661 - 7666

Published: Oct. 16, 2023

A catalyst-free approach for the multicomponent aminoheteroarylation reaction of alkenes with N-aminopyridinium salts and heteroarenes is herein described. The shows good functional group tolerance allows generation valuable β-heteroarylethylamines in satisfying yields. In this transformation, are utilized to generate electron donor–acceptor complexes, which undergo a single-electron transfer process upon light irradiation form key amidyl radicals heteroaryl radical cations. subsequently captured by alkenes, followed Minisci-type yield desired β-heteroarylamines as products.

Language: Английский

Citations

16
Photo-induced imino functionalizations of alkenes via intermolecular charge transfer DOI Creative Commons
Xiang‐Xin Zhang,

Hao Zheng,

Yong‐Kang Mei

et al.

Chemical Science, Journal Year: 2023, Volume and Issue: 14(40), P. 11170 - 11179

Published: Jan. 1, 2023

A catalyst-free photosensitized strategy has been developed for regioselective imino functionalizations of alkenes via the formation an EDA complex. This photo-induced protocol facilitates construction structurally diverse β-imino sulfones and vinyl in moderate to high yields. Mechanistic studies reveal that reaction is initiated with intermolecular charge transfer between oximes sulfinates, followed by fragmentation generate a persistent iminyl radical transient sulfonyl radical. also features excellent regioselectivity, broad functional group tolerance mild conditions. The late stage functionalization natural product derived compounds total synthesis some bioactive molecules have demonstrated highlight utility this protocol. Meanwhile, compatibility different donors proved generality strategy.

Language: Английский

Citations

14
C‐H alkylation of heterocycles via light‐mediated palladium catalysis DOI Creative Commons

Sudip Senapati,

Sudhir Kumar Hota,

Lennard Kloene

et al.

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

Published: Oct. 28, 2024

Methods enabling direct C-H alkylation of heterocycles are fundamental importance in the late-stage modification natural products, bioactive molecules, and medicinally relevant compounds. However, there is a scarcity general strategy for variety using commercially available alkyl surrogates. We report an operationally simple palladium-catalyzed halides under visible light irradiation with good scalability functional group tolerance. Our studies suggest that photoinduced proceeds through cascade events comprising, site-selective radical addition, base-assisted deprotonation, oxidation. A combination experiments computations was employed generalization this strategy, which successfully translated towards products pharmaceuticals.

Language: Английский

Citations

5
Recent Progress in C–S Bond Formation via Electron Donor-Acceptor Photoactivation DOI
Sichang Wang, Liting Wang, Jin Cui

et al.

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

This review summarizes recent progress in EDA complex-promoted C–S bond formation using various sulfur-containing substrates under mild conditions via visible light irradiation.

Language: Английский

Citations

0
Recent Advances in Radical Coupling Reactions Directly Involving Bicyclo[1.1.1]pentane (BCP) DOI

Jiayan Jin,

Huimin Yang,

Huan Xiang

et al.

Topics in Current Chemistry, Journal Year: 2025, Volume and Issue: 383(1)

Published: Jan. 18, 2025

Language: Английский

Citations

0
Electron Donor-Acceptor (EDA) Complex-Driven Activation of N-α C—H Bonds DOI

Junfeng Yang,

Yanqiu Zhao,

Lei Shi

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 45(2), P. 559 - 559

Published: Jan. 1, 2025

Language: Английский

Citations

0
Photo-induced 1,2-alkylarylation/cyclization of alkenes, alkyl halides and N-alkylindoles via an EDA-complex DOI
Tao Ju, Min Ge,

Li-Hang Ren

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(5), P. 1412 - 1419

Published: Jan. 1, 2024

Herein, we developed a photo-induced 1,2-alkylarylation and cyclization of alkenes, alkyl halides N -alkylindoles to synthesize indoles derivatives polysubstituted tetrahydrofuran under mild conditions without the use external redox reagents photosensitizers.

Language: Английский

Citations

3
Advances in Photoinduced Minisci-like Reactions DOI

Mario Martos,

Irene Bosque, José C. González‐Gómez

et al.

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

Published: July 29, 2024

Abstract The Minisci reaction, which has been around for more than five decades, is still the preferred tool straightforward alkylation of basic heteroarenes. recent developments in photocatalysis have opened novel pathways radical generation under milder and sustainable conditions. Implementing this approach into reaction renewed interest transformation, attractive per se Medicinal Chemistry. Aspects such as sacrificial oxidants, catalysts, specific conditions should be carefully examined to evaluate practicability protocol. This short review focuses on advances (2020 February 2024) photoinduced Minisci-type reactions, emphasizing sustainability. 1 Introduction 2 Using Noble-Metal-Based Photocatalysts 3 Noble-Metal-Free Methods Sacrificial Oxidants 4 Without 5 Conclusions Perspectives

Language: Английский

Citations

3
A Decarboxylative Cross-Coupling Platform To Access 2-Heteroaryl Azetidines: Building Blocks with Application in Medicinal Chemistry DOI
James T. Brewster,

Samuel D. Randall,

John P. Kowalski

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(49), P. 9123 - 9129

Published: Dec. 7, 2022

Photoredox-transition metal dual catalysis provides a unique platform for constructing sp3-rich chemical matter. Here, we report nickel-catalyzed cross-coupling of commercially available or easily prepared redox-active NHP azetidine-2-carboxylates with heteroaryl iodides to yield 2-heteroaryl azetidines. This "off-the-shelf" approach yielded products amenable diversification giving access novel saturated heterocyclic scaffolds useful medicinal chemistry programs. An alternative mechanism Hantzsch ester within halides and α-amino radicals is also presented.

Language: Английский

Citations

13