Access to Trifluoromethylketones from Alkyl Bromides and Trifluoroacetic Anhydride by Photocatalysis DOI

Hai‐Wu Du,

Yi‐Dan Du,

Xian‐Wang Zeng

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 135(38)

Published: Aug. 3, 2023

Abstract Aliphatic trifluoromethyl ketones are a type of unique fluorine‐containing subunit which play significant role in altering the physical and biological properties molecules. Catalytic methods to provide direct access aliphatic highly desirable yet remain underdeveloped, partially owing high reactivity instability trifluoroacetyl radical. Herein, we report photocatalytic synthesis from alkyl bromides with trifluoroacetic anhydride. The reaction features dual visible‐light halogen‐atom‐transfer catalysis, followed by an enabling radical‐radical cross‐coupling radical stabilized provides straightforward readily available cost‐effective halides anhydride (TFAA).

Language: Английский

Access to Trifluoromethylketones from Alkyl Bromides and Trifluoroacetic Anhydride by Photocatalysis DOI

Hai‐Wu Du,

Yi‐Dan Du,

Xian‐Wang Zeng

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(38)

Published: Aug. 3, 2023

Aliphatic trifluoromethyl ketones are a type of unique fluorine-containing subunit which play significant role in altering the physical and biological properties molecules. Catalytic methods to provide direct access aliphatic highly desirable yet remain underdeveloped, partially owing high reactivity instability trifluoroacetyl radical. Herein, we report photocatalytic synthesis from alkyl bromides with trifluoroacetic anhydride. The reaction features dual visible-light halogen-atom-transfer catalysis, followed by an enabling radical-radical cross-coupling radical stabilized provides straightforward readily available cost-effective halides anhydride (TFAA).

Language: Английский

Citations

16

Cathodically Coupled Electrolysis to Access Biheteroaryls DOI
Tianyu He,

Chaoqiang Liang,

Haoyuan Cheng

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(3), P. 607 - 612

Published: Jan. 11, 2024

An electrochemical approach to biheteroaryls through the coupling of diverse N-heteroarenes with heteroaryl phosphonium salts is reported. The reaction features pH and redox-neutral conditions excellent regioselectivity, as well exogenous air or moisture tolerance. Additionally, a one-pot, two-step protocol can be established realize formal C–H/C–H heteroarenes, thereby greatly expanding substrate availability. utility this method demonstrated late-stage functionalization, total synthesis nitraridine, antifungal activity studies.

Language: Английский

Citations

5

Metal-Free Synthesis of Trifluoromethyl Carbinol-Containing Imidazo[1,2-a]pyridines via Dehydrative Coupling of Imidazo[1,2-a]pyridines with Trifluoroacetaldehyde DOI
Xiaohua Guo, Kai Yang, Zhaowen Liu

et al.

Synthesis, Journal Year: 2024, Volume and Issue: 56(11), P. 1756 - 1764

Published: Jan. 25, 2024

Abstract A facile and efficient method for the synthesis of trifluoromethylated carbinols has been developed from imidazo[1,2-a]pyridines trifluoroacetaldehyde. The direct C(sp2)–H hydroxytrifluoromethylation is successfully implemented at room temperature using HFIP as solvent through dehydrative cross-coupling process, which displays a broad substrate scope functional group tolerance. Furthermore, gram-scale synthetic transformation experiments have also demonstrated, indicate its potential applicable values in organic synthesis. This green protocol features operational simplicity, atom economy, mild reaction conditions (e.g., temperature, transition-metal- oxidant-free, without inert gas protection), wide scope, excellent practicality.

Language: Английский

Citations

4

Cathodic tandem alkylation/dearomatization of heterocycles enabled by Al-facilitated carbonyl deoxygenation DOI Creative Commons
Jinhui Hu,

Weijie Deng,

Jianfeng Zhou

et al.

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: Jan. 25, 2025

Language: Английский

Citations

0

Recent Advances toward Electro- and Electrophotochemical 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-Catalyzed C—H/C—F Bonds Functionalization DOI
Yongmei Li,

Liangbo Sun,

Kun Xu

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 45(2), P. 668 - 668

Published: Jan. 1, 2025

Language: Английский

Citations

0

Electroreductively driven C–H functionalization of arenes DOI
Pengfei Xie,

Anzai Shi,

Youai Qiu

et al.

Chem Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 101359 - 101359

Published: April 1, 2025

Language: Английский

Citations

0

HFIP-promoted synthesis of imidazo [1,2-a]pyridines containing CF3-substituted tertiary alcohols at room temperature DOI
Juanjuan Gao, Xiaohua Guo, Zhaowen Liu

et al.

Tetrahedron, Journal Year: 2024, Volume and Issue: 156, P. 133943 - 133943

Published: March 19, 2024

Language: Английский

Citations

3

When transition-metal catalysis meets electrosynthesis: a recent update DOI
Fei Lian, Jiuling Li, Kun Xu

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(22), P. 4390 - 4419

Published: Jan. 1, 2024

The merger of organic electrosynthesis with 3d transition-metal catalysis has offered huge opportunities for modern synthesis. This review summarizes the key advancements in this direction published recent two years.

Language: Английский

Citations

3

Acceptorless cross-dehydrogenative coupling for C(sp3)-H heteroarylation mediated by a heterogeneous GaN/ketone photocatalyst/photosensitizer system DOI Creative Commons
Hyotaik Kang, Lida Tan, Jing‐Tan Han

et al.

Communications Chemistry, Journal Year: 2023, Volume and Issue: 6(1)

Published: Sept. 1, 2023

Alkanes are naturally abundant chemical building blocks that contain plentiful C(sp3)-H bonds. While inert, the activation of via hydrogen atom abstraction (HAT) stages an appealing approach to generate alkyl radicals. However, prevailing shortcomings include excessive use oxidants and alkanes impede scope. We herein show gallium nitride (GaN) as a non-toxic, recyclable, heterogeneous photocatalyst enable in conjunction with catalytic simple photosensitizer, benzophenone, promote desired radical generation. The dual photocatalytic cycle enables cross-dehydrogenative Minisci alkylation under mild oxidant-free conditions.

Language: Английский

Citations

9

Electrochemical Decarboxylative Minisci-Type Acylation of Quinoxalines under Catalyst- and External-Oxidant-Free Conditions DOI
Sen Liang, Kun Xu, Cheng‐Chu Zeng

et al.

Synthesis, Journal Year: 2023, Volume and Issue: 55(18), P. 3026 - 3032

Published: Aug. 2, 2023

Abstract An electrochemical approach for the Minisci-type acylation of quinoxalines with α-keto acids as acyl radical precursors is reported. With assistance TFA key additive, acylated were constructed in synthetically useful yields. The distinguishable features this protocol include catalyst- and external oxidant-free conditions, operational simplicity.

Language: Английский

Citations

5