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

Yanmin Fan,

Zhonghou Huang,

Yi Lu

и другие.

Angewandte Chemie, Год журнала: 2023, Номер 136(5)

Опубликована: Дек. 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.

Язык: Английский

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

Yanmin Fan,

Zhonghou Huang,

Yi Lu

и другие.

Angewandte Chemie International Edition, Год журнала: 2023, Номер 63(5)

Опубликована: Дек. 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.

Язык: Английский

Процитировано

17
A Modular Three-Component Approach for Site-selective Tandem Arene Thiophosphorylation DOI
Ziyu Gan, Shuyang Liu, Jia‐Jin Jason Chen

и другие.

Organic Letters, Год журнала: 2024, Номер 26(34), С. 7155 - 7160

Опубликована: Авг. 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.

Язык: Английский

Процитировано

3
Photoinduced Phosphoniumation of Aryl Halides and Arylthianthrenium Salts via an Electron Donor–Acceptor Complex DOI
Ziyu Gan, Jia‐Jin Jason Chen, Han Wang

и другие.

Organic Letters, Год журнала: 2024, Номер 26(36), С. 7751 - 7756

Опубликована: Сен. 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.

Язык: Английский

Процитировано

3
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

и другие.

Journal of Molecular Structure, Год журнала: 2025, Номер unknown, С. 141472 - 141472

Опубликована: Янв. 1, 2025

Язык: Английский

Процитировано

0
NBS-mediated C(sp3)–H amidation of N,N-dimethylamides with N-acyloxyamides DOI
Shuangqing Li, Xiufang Xu,

Gerald Z. Yin

и другие.

Chemical Communications, Год журнала: 2025, Номер unknown

Опубликована: Янв. 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.

Язык: Английский

Процитировано

0
Metal and Photocatalyst-Free Amide Synthesis via Decarbonylative Condensation of Alkynes and Photoexcited Nitroarenes DOI

R. Cui,

Qian Liao,

Yuanxia Zhao

и другие.

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Сен. 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.

Язык: Английский

Процитировано

2
Photocatalysed C–H amidation of indoles enabled by tert-butyl alkyl((perfluoropyridin-4-yl)oxy)carbamate DOI

Ke-Yi Deng,

Zhiwei Wang, Zhenzhen Xie

и другие.

Chemical Communications, Год журнала: 2023, Номер 59(76), С. 11401 - 11404

Опубликована: Янв. 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.

Язык: Английский

Процитировано

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

Chunzheng Ma,

Yuanyuan Chang,

J.‐M. Yang

и другие.

Green Synthesis and Catalysis, Год журнала: 2024, Номер unknown

Опубликована: Окт. 1, 2024

Язык: Английский

Процитировано

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

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(19), С. 13825 - 13837

Опубликована: Сен. 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.

Язык: Английский

Процитировано

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

Yanmin Fan,

Zhonghou Huang,

Yi Lu

и другие.

Angewandte Chemie, Год журнала: 2023, Номер 136(5)

Опубликована: Дек. 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.

Язык: Английский

Процитировано

0