Visible-Light-Promoted [4π + 2σ] Annulation of Dienes and Alkylamines via Dual Inert C(sp3)–H Bond Activation DOI
Shuzhong Wang,

Nuowen Zheng,

Cuo Deji

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(22), P. 4705 - 4710

Published: May 23, 2024

Herein, visible-light-promoted [4π + 2σ] annulation of dienes and alkylamines was achieved via dual C(sp

Language: Английский

Halogen‐Atom Transfer Enabled Catalytic Enantioselective Coupling to Chiral Trifluoromethylated Alkynes via Dual Nickel and Photocatalysis DOI

Shanya Lu,

Zihao Hu,

Dong Wang

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(28)

Published: April 15, 2024

With halogen-atom transfer as an effective tool, a novel catalytic enantioselective protocol to generate chiral trifluoromethylated alkynes has been established by cooperative photoredox and nickel catalysis system, providing straightforward modular route access this type of product in good yields enantioselectivities. The process is essential for the reaction strategy offers another promising way utilize alkyl halides with highly negative reduction potentials. It firstly expands nickel-catalyzed asymmetric reductive cross-couplings organohalides from traditional single-electron transfer.

Language: Английский

Citations

10

Multicomponent Construction of Tertiary Alkylamines by Photoredox/Nickel-Catalyzed Aminoalkylation of Organohalides DOI
Tao Yang,

Wenhui Xiong,

Guangyu Sun

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(42), P. 29177 - 29188

Published: Oct. 12, 2024

Tertiary alkylamines are privileged structural motifs widely present in natural products, pharmaceutical agents, and bioactive molecules, their efficient synthesis has been a longstanding goal organic chemistry. The functionalization of α-amino radicals derived from abundant precursors represents an emerging approach to accessing alkylamines, but application this strategy obtain tertiary remains challenging. Here, we show that dual photoredox/nickel catalysis enables aminoalkylation organohalides (sp

Language: Английский

Citations

6

Direct Synthesis of β-Amino Boronates via Amide α-C–H Bond Activation and C(sp3)–C(sp3) Coupling under Dual Ni/Photoredox Catalysis DOI

Zihao Hu,

Dong Wang, Tao Xu

et al.

ACS Catalysis, Journal Year: 2023, Volume and Issue: 14(1), P. 547 - 553

Published: Dec. 26, 2023

Direct transformations of readily available amines or amides via C–H bond functionalization could provide a fast route for accessing complex molecules. While various groups have been successfully incorporated into the α position nitrogen atom with photoredox system activation, couplings functionalized alkyl halides are still very challenging. Herein, we report direct and convenient protocol β-amino boronates through C(sp3)–C(sp3) coupling α-bromoboronates. The mild conditions allow good functional group tolerance broad scope. application method in late-stage modification molecules further demonstrates its great potential organic synthesis. Mechanistic studies were also conducted, catalytic cycle is proposed.

Language: Английский

Citations

10

Thermodynamic H-Abstraction Abilities of Nitrogen Centered Radical Cations as Potential Hydrogen Atom Transfer Catalysts in Y–H Bond Functionalization DOI Creative Commons
Xia Zhao, Yilin Hou,

Bao‐Chen Qian

et al.

ACS Omega, Journal Year: 2024, Volume and Issue: 9(24), P. 26708 - 26718

Published: June 4, 2024

Y–H bond functionalization has always been the focus of research interest in area organic synthesis. Direct hydrogen atom transfer (HAT) from is one most efficient and practical methods to activate bond. Recently, nitrogen centered radical cations were broadly utilized as H-abstraction catalysts bonds via HAT process. As a type catalyst, H-affinity significant thermodynamic parameter quantitatively evaluate potentials cations. In this work, pKa values 120 protonated N-containing compounds acetonitrile (AN) are predicted, H-affinities AN derived reduction using Hess' law. This work focuses on abilities enrich molecule library novel or H-abstractors provides valuable guidelines for application functionalization.

Language: Английский

Citations

3

Photochemical Radical Cascade 6‐endo Cyclization of Dienes with α‐Carbonyl Bromides for the Synthesis of Six‐Membered Benzo‐Fused Lactams DOI

Jia‐Li Sui,

Yang Guo, Biquan Xiong

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(19), P. 2323 - 2328

Published: May 22, 2024

Comprehensive Summary A novel visible‐light‐induced radical cascade 6‐ endo cyclization of dienes ( N ‐(2‐vinylphenyl)acryl amides) is developed utilizing α‐carbonyl bromides as alkyl reagents. This approach affords an efficient way for synthesizing six‐membered benzo‐fused lactam derivatives with chemo‐ and regio‐selectivity good functional group tolerance. Primary, secondary, tertiary are well‐compatible this reaction.

Language: Английский

Citations

2

Visible Light Catalyzed Reductive Cross‐Coupling of αCF3‐alkyl Bromide and Alkynyl Bromide DOI

Yiqiang Tian,

Yi Li, Chun Zhang

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(20), P. 2479 - 2484

Published: June 21, 2024

Comprehensive Summary Traditional reduction coupling reactions of two bromides typically rely on transition metal catalysis. Here, we introduce the development a visible‐light catalytic direct reaction between α ‐CF 3 ‐alkyl and alkynyl to access valuable organic frameworks. Our research confirms excellent compatibility this with various functional groups, which could be used modify substrate biologically active molecular fragments. Mechanistic investigations, including control experiments, fluorescence quenching studies, light‐switching have provided insights into mechanism. This study paves way for application catalysis in diverse synthetic transformations, offering sustainable efficient approach synthesis.

Language: Английский

Citations

2

Light‐Mediated Radical Addition to Azomethine Compounds: Novel Reactivity and Activation Modes DOI Open Access

Zakhar M. Rubanov,

Vitalij V. Levin, Alexander D. Dilman

et al.

The Chemical Record, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 17, 2024

Abstract Azomethines is a class of compounds, which have traditionally served as electrophilic substrates, but their reactions with radicals long been limited. Photocatalysis provided ample opportunities for promoting these reactions, wide variety reagents serving precursors radicals. Besides regular addition mode at the azomethine fragment, oxidative pathway, in C=N bond remains product, has become possible by proper selection redox catalyst. This review summarizes new developments this rapidly developing field over past five years. New concepts on activation towards radical attack are discussed.

Language: Английский

Citations

2

Halogen‐Atom Transfer Enabled Catalytic Enantioselective Coupling to Chiral Trifluoromethylated Alkynes via Dual Nickel and Photocatalysis DOI

Shanya Lu,

Zihao Hu,

Dong Wang

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(28)

Published: April 15, 2024

Abstract With halogen‐atom transfer as an effective tool, a novel catalytic enantioselective protocol to generate chiral trifluoromethylated alkynes has been established by cooperative photoredox and nickel catalysis system, providing straightforward modular route access this type of product in good yields enantioselectivities. The process is essential for the reaction strategy offers another promising way utilize alkyl halides with highly negative reduction potentials. It firstly expands nickel‐catalyzed asymmetric reductive cross‐couplings organohalides from traditional single‐electron transfer.

Language: Английский

Citations

1

2H-Thiazolo[4,5-d][1,2,3]triazole: synthesis, functionalization, and application in scaffold-hopping DOI Creative Commons

Ryuya Miyazaki,

Fumito Takada,

Takunari Kikuchi

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(38), P. 15835 - 15840

Published: Jan. 1, 2024

We have developed 2 H -thiazolo[4,5- d ][1,2,3]triazole (ThTz), an unprecedented [5-5]-fused heteroaromatic system for medicinal chemistry. C5-sulfonylated ThTz has been commercialized through Tokyo Chemical Industry Ltd (TCI: catalogue number M3881).

Language: Английский

Citations

0

Photoredox-Catalyzed C–H Methylation of N-Heteroarenes Enabled by N,N-Dimethylethanolamine DOI
Jiayang Wang, Yun Wang, Wei-Yang Lin

et al.

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

Published: Nov. 21, 2024

A visible-light-driven radical C-H methylation of

Language: Английский

Citations

0