SbCl3-Initiated Csp3 –Csp3 Coupling between N-Aryltetrahydroisoquinolines and Nitroalkanes via the Aerobic Oxidation of sp3 C–H Bond DOI
Yu Yuan, Xiaodong Jia,

Qiyuan Ma

et al.

Synthesis, Journal Year: 2023, Volume and Issue: 55(10), P. 1593 - 1601

Published: Jan. 12, 2023

Abstract An SbCl3-initiated Csp3 –Csp3 coupling between N-aryltetrahydroisoquinolines and nitromethanes was realized through the aerobic oxidation of sp 3 C–H bond, providing a series nitromethylated tetrahydroisoquinoline derivatives in high yields. The results exhibited that SbCl3, as cheap commercially available reagent, is an efficient initiator to promote direct functionalization sp3 bond with broad functional group tolerance, which potentially applied wider range activation reactions.

Language: Английский

Electrochemical radical-polar crossover: a radical approach to polar chemistry DOI

Zhoumei Tan,

Haonan Zhang, Kun Xu

et al.

Science China Chemistry, Journal Year: 2023, Volume and Issue: 67(2), P. 450 - 470

Published: Nov. 3, 2023

Language: Английский

Citations

50

Aryl sulfonium salt electron donor-acceptor complexes for halogen atom transfer: Isocyanides as tunable coupling partners DOI Creative Commons
Huaibo Zhao,

Valentina Dafnae Cuomo,

James A. Rossi‐Ashton

et al.

Chem, Journal Year: 2024, Volume and Issue: 10(4), P. 1240 - 1251

Published: Feb. 13, 2024

The photoactivation of sulfonium salt EDA (electron donor-acceptor) complexes provides a mild platform for aryl-radical-mediated halogen atom transfer activation wide range functionalized alkyl iodides, including tertiary iodides. Using an aryl with carbonate as inexpensive donor complex formation, the general reaction has been applied in divergent, metal-free photochemical approach to nitriles and amides. This divergency was made possible by tuning isocyanide radical traps. For example, identification readily accessible, bench-stable, crystalline amide containing grants access nitrile products complete selectivity.

Language: Английский

Citations

16

Cyanation with isocyanides: recent advances and perspectives DOI

Yingying Shan,

Xun Zhang,

Gongle Liu

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(12), P. 1546 - 1562

Published: Jan. 1, 2024

This review focuses on the cyanation of isocyanides with recent advances and perspectives.

Language: Английский

Citations

11

Electrochemical Benzylic C(sp3)–H Acyloxylation DOI Creative Commons
Alexander Atkins, Albert C. Rowett, David M. Heard

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(28), P. 5105 - 5108

Published: July 13, 2022

The development of sustainable C(sp3)–H functionalization methods is great interest to the pharmaceutical and agrochemical industries. Anodic oxidation an efficient means producing benzylic cations that can undergo subsequent in situ nucleophilic attack afford functionalized products. Herein, we demonstrate suitability carboxylic acids as nucleophiles yield esters. This method employs a series secondary substrates demonstrated on gram scale flow.

Language: Английский

Citations

36

Recent Advances on C—H Functionalization via Oxidative Electrophotocatalysis DOI

Aman Hasil,

Rui Chang,

Juntao Ye

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(3), P. 728 - 728

Published: Jan. 1, 2024

Language: Английский

Citations

8

Chemo‐ and Site‐Selective Electro‐Oxidative Alkane Fluorination by C(sp3)−H Cleavage DOI Creative Commons
Maximilian Stangier, Alexej Scheremetjew, Lutz Ackermann

et al.

Chemistry - A European Journal, Journal Year: 2022, Volume and Issue: 28(60)

Published: July 18, 2022

Electrochemical fluorinations of C(sp

Language: Английский

Citations

24

S-alkyl Dithiocarbamates Synthesis through Electrochemical Multicomponent Reaction of Thiols, Hydrogen Sulfide, and Isocyanides DOI
Xiaoying Liu,

Tian-Cheng Cai,

Mengxue Zhu

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(17), P. 12311 - 12318

Published: Aug. 16, 2023

Dithiocarbamates synthesis is extremely important in plenty of biomedical and agrochemical applications, especially fungicide development, but remains a great challenge. In this work, we have successfully developed multicomponent reaction protocol to convert H2S into S-alkyl dithiocarbamates under constant current conditions. No additional oxidants nor catalysts are required, due mild conditions, the reactions display broad substrate scope, including varieties thiols or disulfides.

Language: Английский

Citations

12

Nickel-Catalyzed Reductive Amidation of Aryl Fluorosulfates with Isocyanates: Synthesis of Amides via C–O Bond Cleavage DOI

Gan‐Qi Qin,

Jiao Wang,

Xu-Rong Cao

et al.

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

Published: Aug. 30, 2024

With the assistance of nickel as catalyst, 2,2'-bipyridine (bpy) ligand, and manganese reducing metal, reductive amidation isocyanates with readily accessible aryl fluorosulfates could be successfully accomplished. The reactions proceeded effectively via C-O bond activation in DMF at room temperature, enabling facile synthesis a range structurally diverse amides moderate to high yields broad functionality compatibility. In addition, synthetic usefulness method was further demonstrated by applying reaction scale-up late-stage functionalization complex molecules biological activities.

Language: Английский

Citations

4

Recent Advances in the Electrochemical Functionalization of Isocyanides DOI

Qingyun Gu,

Zhenfeng Cheng,

Xiaodong Qiu

et al.

The Chemical Record, Journal Year: 2022, Volume and Issue: 23(1)

Published: Sept. 20, 2022

Abstract Isocyanides are well‐known as efficient CO surrogates and C1 synthons in modern organic synthesis. Although tremendous efforts have been devoted to fully exploiting the reactivity of isocyanides, these transformations primarily limited by their utilization stoichiometric toxic chemical oxidants. With recent resurgence electrochemistry, which has considerably laid dormant over past several decades, electrolysis identified a green powerful tool enrich structural diversity solely utilizing electric current clean inherently safe redox equivalents In this regard, unique isocyanides studied numerous electrochemical transformations. This review comprehensively highlights most relevant progress strategies towards functionalization up until June 2022, with focus on reaction outcomes mechanisms.

Language: Английский

Citations

15

Diverse C(sp3)–H functionalizations through electrochemical benzylic oxygenation DOI
Yan He, Tiansheng Chen, Xuesen Fan

et al.

Organic Chemistry Frontiers, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Reported herein is a transition metal catalyst- and oxidant-free platform for diversity-oriented benzylic C–H functionalization. The process involves electrochemical C(sp 3 )–H oxygenation followed by elimination/substitution with diverse nucleophiles.

Language: Английский

Citations

0