Defluorinative Alkylboration of Alkenes Enabled by Dual Photoredox and Copper Catalysis DOI

Yanmin Fan,

Zhonghou Huang,

Yi Lu

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 136(5)

Published: Dec. 9, 2023

Abstract A regioselectivity reversed three‐component defluorinative alkylboration of alkenes with trifluoromethyls and bis(pinacolato)diboron via dual photoredox/copper catalysis is reported. The mild conditions are compatible a wide array nonactivated trifluoromethyl aromatics bearing electron‐donating or electron‐neutral substituents, trifluoroacetamides, various terminal internal alkenes, enabling straightforward access to synthetically valuable γ ‐ gem ‐difluoroalkyl boronates high efficiency. Furthermore, this protocol applicable alkene‐tethered furnish ‐difluoromethylene‐containing cyclic compounds. Synthetic applications preliminary mechanistic studies also presented.

Language: Английский

Defluorinative Alkylboration of Alkenes Enabled by Dual Photoredox and Copper Catalysis DOI Open Access

Yanmin Fan,

Zhonghou Huang,

Yi Lu

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 63(5)

Published: Dec. 9, 2023

Abstract A regioselectivity reversed three‐component defluorinative alkylboration of alkenes with trifluoromethyls and bis(pinacolato)diboron via dual photoredox/copper catalysis is reported. The mild conditions are compatible a wide array nonactivated trifluoromethyl aromatics bearing electron‐donating or electron‐neutral substituents, trifluoroacetamides, various terminal internal alkenes, enabling straightforward access to synthetically valuable γ ‐ gem ‐difluoroalkyl boronates high efficiency. Furthermore, this protocol applicable alkene‐tethered furnish ‐difluoromethylene‐containing cyclic compounds. Synthetic applications preliminary mechanistic studies also presented.

Language: Английский

Citations

17
NBS-mediated C(sp3)–H amidation of N,N-dimethylamides with N-acyloxyamides DOI
Shuangqing Li, Xiufang Xu,

Gerald Z. Yin

et al.

Chemical Communications, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Efficient synthesis of methylenebisamides was achieved by NBS-mediated amidation C(sp 3 )–H bonds adjacent to the nitrogen in N , -dimethylamides with -acyloxyamides.

Language: Английский

Citations

0
Iron-catalyzed direct N-methylation of N-methoxy benzamides: A solvent-free approach to bisamides utilizing the methoxy group as a “build-in” methylene donor DOI
Dandan Jiang, Jun Xiao,

Lai-Xi Zou

et al.

Journal of Molecular Structure, Journal Year: 2025, Volume and Issue: unknown, P. 141472 - 141472

Published: Jan. 1, 2025

Language: Английский

Citations

0
Photoinduced Phosphoniumation of Aryl Halides and Arylthianthrenium Salts via an Electron Donor–Acceptor Complex DOI
Ziyu Gan, Jia‐Jin Jason Chen, Han Wang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(36), P. 7751 - 7756

Published: Sept. 5, 2024

Owing to their remarkable practicality and utility, phosphonium salts have attracted substantial interest are widely applied in critical areas, such as medicine, materials science, catalysis. Herein, we developed a facile photocatalyst/metal-free synthetic strategy for the preparation of utilizing aryl halides/arylthianthrenium radical precursors. This approach is disclosed undergo an efficient light-induced electron donor-acceptor pathway, facilitating synthesis structurally diverse range salts.

Language: Английский

Citations

2
A Modular Three-Component Approach for Site-selective Tandem Arene Thiophosphorylation DOI
Ziyu Gan,

Shuyang Liu,

Jia‐Jin Jason Chen

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(34), P. 7155 - 7160

Published: Aug. 21, 2024

Thiophosphates serve as pivotal reagents within the realms of both organic and inorganic synthesis, with their most notable applications observed in agricultural chemistry. This manuscript delineates a modular three-component synthetic strategy for site-selective arene C–H thiophosphorylation thianthrenium salt, 1,4-diazabicyclo[2.2.2]octane-sulfur dioxide (DABSO), diarylphosphine oxides substrates. approach facilitates metal-free green synthesis diverse spectrum S-aryl phosphorothioates through functionalization late-stage modification showcasing practicality broad applicability.

Language: Английский

Citations

1
Recent advances in photocatalytic C-H amination to nitrogenous structures DOI Creative Commons

Chunzheng Ma,

Yuanyuan Chang,

J.‐M. Yang

et al.

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

Published: Oct. 1, 2024

Language: Английский

Citations

0
Photocatalysed C–H amidation of indoles enabled by tert-butyl alkyl((perfluoropyridin-4-yl)oxy)carbamate DOI

Ke-Yi Deng,

Zhiwei Wang, Zhenzhen Xie

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(76), P. 11401 - 11404

Published: Jan. 1, 2023

A new photoinduced amidation protocol was developed by utilizing the readily available tert -butyl alkyl((perfluoropyridin-4-yl)oxy)carbamate as an effective amidyl radical precursor under mild conditions.

Language: Английский

Citations

1
Metal and Photocatalyst-Free Amide Synthesis via Decarbonylative Condensation of Alkynes and Photoexcited Nitroarenes DOI

R. Cui,

Qian Liao,

Yuanxia Zhao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 24, 2024

Depending on the intrinsic photoactivity of nitroarenes, we herein developed a practical Brønsted acid-catalyzed decarbonylative amide synthesis from alkynes and photoexcited nitroarenes without any metal or photocatalyst. This method exhibited compatibility with water air, broad substrate applicability, marvelous functional group tolerance, wide applications in scale-up synthesis, late-stage functionalization, total synthesis. Mechanism studies DFT calculations supported that 1,3,2-dioxazole intermediate was involved, gaseous carbon monoxide only byproduct during construction.

Language: Английский

Citations

0
Metal-Free Selective Ortho-C–H Amidation of Hypervalent(III) Iodobezenes with N-Methoxy Amides under Mild Conditions DOI
Wei‐Hao Rao,

Ying‐Ge Li,

Lili Jiang

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(19), P. 13825 - 13837

Published: Sept. 22, 2023

A metal-free selective ortho-C-H amidation of aryl iodines(III) with the use N-methoxy amides as aminating reagents under mild conditions is described here. In protocol, excellent chemoselectivity and high regioselectivity were obtained. Notably, iodine substituent rendered product suitable to be used for further elaboration.

Language: Английский

Citations

0
Defluorinative Alkylboration of Alkenes Enabled by Dual Photoredox and Copper Catalysis DOI

Yanmin Fan,

Zhonghou Huang,

Yi Lu

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 136(5)

Published: Dec. 9, 2023

Abstract A regioselectivity reversed three‐component defluorinative alkylboration of alkenes with trifluoromethyls and bis(pinacolato)diboron via dual photoredox/copper catalysis is reported. The mild conditions are compatible a wide array nonactivated trifluoromethyl aromatics bearing electron‐donating or electron‐neutral substituents, trifluoroacetamides, various terminal internal alkenes, enabling straightforward access to synthetically valuable γ ‐ gem ‐difluoroalkyl boronates high efficiency. Furthermore, this protocol applicable alkene‐tethered furnish ‐difluoromethylene‐containing cyclic compounds. Synthetic applications preliminary mechanistic studies also presented.

Language: Английский

Citations

0