Direct Substitution of 2‐Aminotropones with Potassium Allyltrifluoroborates through Transition‐Metal‐Free C–N Bond Cleavage DOI
Qianqian Wu, Yan Wang, Muliang Zhang

et al.

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 13(11)

Published: Aug. 28, 2024

Abstract The poor nucleofugality of the amino group renders C−N bond functionalization primary aromatic amines highly challenging. Herein, we report a direct substitution reaction 2‐aminotropones, bearing unique non‐benzenoid seven‐membered ring that exists in some natural products and bioactive molecules, with potassium allyltrifluoroborates through cleavage under transition‐metal‐free conditions. 2‐aminotropones were directly substituted presence sodium bicarbonate, delivering structurally diverse 2‐allyltropones moderate to good yields. is free directing groups, activating groups transition metals, providing convenient method access tropones.

Language: Английский

The Strategies towards Electrochemical Generation of Aryl Radicals DOI
Xiaobao Zeng

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: unknown

Published: July 16, 2024

The advancement in electrochemical techniques has unlocked a new path for achieving unprecedented oxidations and reductions of aryl radical precursors controlled selective manner. This approach facilitates the construction aromatic carbon-carbon carbon-heteroatom bonds. In light green merits growing importance this technique chemistry, review aims to provide an overview recent advance generation radicals organized by precursor type, with focus on substrate scope, limitation, underlying mechanism, thereby inspiring future work generation.

Language: Английский

Citations

9
Nickel-Catalyzed Inter- and Intramolecular Reductive Cross-Coupling Reactions of Arylbenzylammonium Salts through Highly Site-Selective C–N Bond Cleavage DOI

Ren-Gui Tian,

Longyu Wang,

Linze Zheng

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(7), P. 5039 - 5046

Published: March 20, 2024

The site selectivity has been investigated for the C–N bond cleavage of arylbenzylammonium salts in reductive cross-coupling reactions with carbon electrophiles. A wide variety triflates participated nickel-catalyzed zinc-mediated benzyl–aryl cross-electrophile coupling aryl bromides to afford diarylmethanes extremely high selectivity. same reaction conditions were successfully extended intramolecular benzyl(bromoaryl)ammonium triflates. Moreover, underwent manganese-mediated benzyl–acyl aromatic carboxylic acids presence di-tert-butyl pyrocarbonate. These employ readily available feedstocks and reagents, exhibit benzylic bonds rather than bonds, tolerate a functional groups.

Language: Английский

Citations

6
Modern photo- and electrochemical approaches to aryl radical generation DOI Creative Commons

Krzysztof Grudzień,

Andrei Zlobin,

Jan Zadworny

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(18), P. 5232 - 5277

Published: Jan. 1, 2024

This review describes recent advances in the generation of aryl radicals using light and electricity. Such modern techniques allow for efficient energy resource utilization, thus providing more sustainable radical arylation methods.

Language: Английский

Citations

6
Strategies for Using Quaternary Ammonium Salts as Alternative Reagents in Alkylations DOI Creative Commons
Johanna Templ, Michael Schnürch

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(33)

Published: April 8, 2024

Alkylation reactions are pivotal in organic chemistry, with wide-ranging utilization across various fields of applied synthetic chemistry. However, conventional reagents employed alkylations often pose substantial health and exposure risks. Quaternary ammonium salts (QAS) present a promising alternative for these transformations offering significantly reduced hazards as they non-cancerogenic, non-mutagenic, non-flammable, non-corrosive. Despite their potential, use direct remains relatively unexplored. This review outlines strategies utilizing QAS alkylation reactions, providing researchers safer approaches to chemical synthesis.

Language: Английский

Citations

3
A Practical Electrochemical Approach for Synthesizing Selenyl-Dihydrobenzofurans and Chromane with a Tetrasubstituted Carbon Center DOI
Xianqiang Kong, Xiaohong Chen, Zhong‐Yan Cao

et al.

Synthesis, Journal Year: 2024, Volume and Issue: 56(17), P. 2695 - 2702

Published: June 24, 2024

Abstract A straightforward and efficient electrochemical method for the anodic oxidative selenenylation of 2-(2-arylallyl)phenols a 2-(3-arylbut-3-en-1-yl)phenol with diselenides under ambient air conditions has been outlined. This allows synthesis selenyl-dihydrobenzofurans chromane featuring sterically hindered tetrasubstituted carbon center, demonstrated through 25 examples yields reaching up to 98%. Initial mechanistic investigations suggest likely participation pivotal seleniranium cation species in regulating reactivity.

Language: Английский

Citations

2
Nickel-Catalyzed Reductive Cross-Coupling of Allylammonium Salts with Alkyl Iodides DOI

Jia-Jia Liao,

Ren-Gui Tian,

Shi‐Kai Tian

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(20), P. 14781 - 14788

Published: Sept. 28, 2023

An unprecedented reductive cross-coupling reaction of allylammonium salts with alkyl electrophiles has been established through C-N bond cleavage. A range bromides smoothly participated in the nickel-catalyzed zinc-mediated allyl-alkyl cross-electrophile coupling iodides, delivering structurally diverse alkene products moderate to good yields high linear selectivity. Preliminary mechanistic experiments are consistent formation an radical from iodide.

Language: Английский

Citations

3
Electrochemical oxidative transamidation of tertiary amines with N-acyl imides to access amide compounds DOI

Hai Lin,

Shengzhang Liu,

Qing Li

et al.

Synthetic Communications, Journal Year: 2023, Volume and Issue: 53(17), P. 1412 - 1425

Published: June 27, 2023

A novel and efficient electrochemical oxidative transamidation of tertiary amines with N-acyl imides is described. This protocol environmentally friendly ease to handle as are used surrogates for secondary amines. The C-N bond cleaved, preparing amide compounds in a facile approach 29 examples 11–80% yields.

Language: Английский

Citations

2
Advances in Electrochemical Cathodic Reductive Reactions Involving Carbon-Nitrogen Bonds DOI
Jian Huang, Wen‐Zhen Zhang

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(3), P. 825 - 825

Published: Jan. 1, 2024

Language: Английский

Citations

0
Electrochemical Organic Synthesis DOI
Hai‐Chao Xu

Synthesis, Journal Year: 2023, Volume and Issue: 55(18), P. 2797 - 2798

Published: Aug. 29, 2023

Received: 03 August 2023 Accepted after revision: Article published online:29

Language: Английский

Citations

1
Direct Substitution of 2‐Aminotropones with Potassium Allyltrifluoroborates through Transition‐Metal‐Free C–N Bond Cleavage DOI
Qianqian Wu, Yan Wang, Muliang Zhang

et al.

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 13(11)

Published: Aug. 28, 2024

Abstract The poor nucleofugality of the amino group renders C−N bond functionalization primary aromatic amines highly challenging. Herein, we report a direct substitution reaction 2‐aminotropones, bearing unique non‐benzenoid seven‐membered ring that exists in some natural products and bioactive molecules, with potassium allyltrifluoroborates through cleavage under transition‐metal‐free conditions. 2‐aminotropones were directly substituted presence sodium bicarbonate, delivering structurally diverse 2‐allyltropones moderate to good yields. is free directing groups, activating groups transition metals, providing convenient method access tropones.

Language: Английский

Citations

0