scholarly journals Construction of sterically congested oxindole derivatives via visible-light-induced radical-coupling

2021 ◽  
Author(s):  
Yanling Shen ◽  
Ning Lei ◽  
Cong Lu ◽  
Dailin Xi ◽  
Xinxin Geng ◽  
...  
Keyword(s):  
Visible Light ◽  
Functional Group ◽  
Modular Assembly ◽  
Radical Coupling ◽  
Mild Conditions ◽  
Broad Scope

Simple, modular assembly of complex fluoroalkyl-containing oxindole derivatives with a broad scope and excellent functional group tolerance under mild conditions (metal- and photocatalyst-free). Benzyl iodides were identified as key intermediates.

Enantioselective Radical Functionalization of Imines and Iminium Intermediates via Visible Light Photoredox Catalysis

Synthesis ◽  
2020 ◽  
Author(s):  
Jia-Jia Zhao ◽  
Hong-Hao Zhang ◽  
Shouyun Yu
Keyword(s):  
Visible Light ◽  
Asymmetric Synthesis ◽  
Carbonyl Compounds ◽  
Asymmetric Reduction ◽  
Chemical Transformations ◽  
Photoredox Catalysis ◽  
Radical Coupling ◽  
Mild Conditions ◽  
Iminium Ions ◽  
Radical Functionalization

Visible light photoredox catalysis has recently emerged as a powerful tool for the development of new and valuable chemical transformations under mild conditions. Visible-light promoted enantioselective radical transformations of imines and iminium intermediates provide new opportunities for the asymmetric synthesis of amines and asymmetric β-functionalization of unsaturated carbonyl compounds. In this review, the advance in the catalytic asymmetric radical functionalization of imines, as well as iminium intermediates, are summarized. 1 Introduction 2 The enantioselective radical functionalization of imines 2.1 Asymmetric reduction 2.2 Asymmetric cyclization 2.3 Asymmetric addition 2.4 Asymmetric radical coupling 3 The enantioselective radical functionalization of iminium ions 3.1 Asymmetric radical alkylation 3.2 Asymmetric radical acylation 4 Conclusion

Bromotrifluoromethane: A Useful Reagent for Hydrotrifluoromethylation of Alkenes and Alkynes

Synlett ◽  
2018 ◽  
Vol 29 (08) ◽  
pp. 1028-1032 ◽  
Author(s):  
Xing Zheng ◽  
Xingang Zhang ◽  
Yu-Yan Ren
Keyword(s):  
Visible Light ◽  
Organic Synthesis ◽  
Functional Group ◽  
Mild Conditions ◽  
Industrial Material ◽  
Reaction Proceeds

Bromotrifluoromethane (CF3Br) is a simple, inexpensive and abundant industrial material employed as a trifluoromethylating reagent. However, only limited strategies using CF3Br as a fluorine source are reported. Herein, we describe a visible-light-induced hydrotrifluoromethylation of alkenes and alkynes with CF3Br. The reaction proceeds under mild conditions with good functional group tolerance, providing a new route for the application of BrCF3 in organic synthesis.

Visible-Light-Induced Radical Polynitration of Arylboronic Acids: Synthesis of Polynitrophenols

Synthesis ◽  
2018 ◽  
Vol 50 (15) ◽  
pp. 2891-2896 ◽  
Author(s):  
Jinna Song ◽  
Xihe Bi ◽  
Qi Zhang ◽  
Kaki Raveendra Babu ◽  
Zhouliang Huang
Keyword(s):  
Visible Light ◽  
Aromatic Compounds ◽  
Functional Group ◽  
Simple Procedure ◽  
One Pot ◽  
Arylboronic Acids ◽  
Mild Conditions ◽  
Conventional Methods ◽  
Straightforward Approach

We report a visible light-assisted one-pot method for the synthesis of polynitrophenols through radical tandem hydroxylation and nitration of arylboronic acids by utilizing copper(II) nitrate tri­hydrate as the nitro source. This method features mild conditions, a simple procedure, and good functional group tolerance. Compared to conventional methods, this work provides a straightforward approach for the polynitration of aromatic compounds.

A mild, general, and metal-free method for site-specific deuteration induced by visible light using D2O as the source of deuterium atoms

2020 ◽  
Vol 22 (3) ◽  
pp. 669-672 ◽  
Author(s):  
Shuai Shi ◽  
Ruining Li ◽  
Liangming Rao ◽  
Zhankui Sun
Keyword(s):  
Visible Light ◽  
Functional Group ◽  
Site Specific ◽  
Metal Free ◽  
Mild Conditions ◽  
Highly Efficient ◽  
Radical Approach

Visible light induced desulfurization–deuteration method was developed using D2O as the source of deuterium atoms. This radical approach features mild conditions, broad substrate scope, highly efficient D-incorporation and excellent functional group compatibility.

Iron(III)/TEMPO-Catalyzed Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles by Oxidative Cyclization under Mild Conditions

Synlett ◽  
2017 ◽  
Vol 28 (11) ◽  
pp. 1373-1377 ◽  
Author(s):  
Chengrong Ding ◽  
Guofu Zhang ◽  
Yidong Yu ◽  
Yiyong Zhao ◽  
Xiaoqiang Xie
Keyword(s):  
Functional Group ◽  
Oxidative Cyclization ◽  
Mild Conditions ◽  
Broad Scope ◽  
Oxadiazole Derivatives ◽  
High Yields

A simple and efficient cationic Fe(III)/TEMPO-catalyzed oxidative cyclization of aroyl hydrazones has been developed for the synthesis of 2,5-disubstituted 1,3,4-oxadiazole derivatives. The reaction offers a broad scope, good functional-group tolerance, and high yields under mild conditions in the presence of O2.

scholarly journals Dual Ni/photoredox-catalyzed asymmetric cross-coupling to access chiral benzylic boronic esters

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Purui Zheng ◽  
Pan Zhou ◽  
Dong Wang ◽  
Wenhao Xu ◽  
Hepan Wang ◽  
...  
Keyword(s):  
Visible Light ◽  
Ambient Temperature ◽  
Functional Group ◽  
Cross Coupling ◽  
Strong Base ◽  
Mild Conditions ◽  
Aryl Iodides ◽  
Boronic Esters

AbstractThe flourishing Ni/photoredox-catalyzed asymmetric couplings typically rely on redox-neutral reactions. In this work, we report a reductive cross-coupling of aryl iodides and α-chloroboranes under a dual catalytic regime to further enrich the metallaphotoredox chemistry. This approach proceeds under mild conditions (visible light, ambient temperature, no strong base) to access the versatile benzylic boronic esters with good functional group tolerance and excellent enantioselectivities.

Late-Stage Alkylation of N-Containing Heteroarenes Enabled by Homolysis of Alkyl-1,4-dihydropyridines under Blue LED Irradiation

Synlett ◽  
2020 ◽  
Author(s):  
Ping Wang ◽  
Xiaoping Chen ◽  
Xiaosheng Luo ◽  
Kaiqian Wang ◽  
Feng Liang
Keyword(s):  
Visible Light ◽  
Late Stage ◽  
Bioactive Molecules ◽  
Blue Led ◽  
Ambient Temperatures ◽  
Mild Conditions ◽  
Broad Scope ◽  
Led Irradiation

AbstractAlkylated heteroarenes are widely found in bioactive molecules and pharmaceuticals. Therefore, there is great interest in developing a chemoselective alkylation of heteroarenes under mild conditions, particularly during a late-stage functionalization step for the purpose of rapid derivatization. Herein, we introduce an efficient visible-light-promoted C–H alkylation of nitrogen-containing heteroarenes by using C4-alkyl 1,4-dihydropyridines (DHPs) as radical precursors at ambient temperatures. A broad scope of heteroarenes, such as 4-hydroxyquinazoline and its derivatives, including those bearing electron-donating or electron-withdrawing groups, can be successfully alkylated in good yields by using various C4-alkyl DHPs.

Iridium(III)-Catalyzed Difluoroalkylation–Bicyclization of 1,7-Enynes toward Benzo[a]fluoren-5-ones under Visible-Light Photoredox Conditions

Synthesis ◽  
2020 ◽  
Vol 52 (24) ◽  
pp. 3865-3873
Author(s):  
Wen-Juan Hao ◽  
Bo Jiang ◽  
Min-Hua Huang
Keyword(s):  
Visible Light ◽  
Functional Group ◽  
High Efficiency ◽  
Mild Conditions ◽  
Wide Range

A new visible-light-induced Ir(III)-catalyzed difluoroalkylation–bicyclization of 1,7-enynes with ethyl 2-bromo-2,2-difluoroacetate (BrCF2CO2Et) is described, furnishing a wide range of difluoromethyl-containing benzo[a]fluoren-5-ones in good to excellent yields. The reaction is operationally simple, proceeds with high efficiency under mild conditions, and shows excellent functional group compatibility.

Visible-light-promoted oxidative desulphurisation: a strategy for the preparation of unsymmetrical ureas from isothiocyanates and amines using molecular oxygen

2020 ◽  
Vol 22 (9) ◽  
pp. 2956-2962 ◽  
Author(s):  
Ziyu Gan ◽  
Guoqing Li ◽  
Qiuli Yan ◽  
Weiseng Deng ◽  
Yuan-Ye Jiang ◽  
...  
Keyword(s):  
Visible Light ◽  
Molecular Oxygen ◽  
Functional Group ◽  
Mild Conditions

A green and efficient visible-light promoted oxidative desulphurisation protocol has been proposed for the construction of unsymmetrical ureas under mild conditions with broad substrate scope and good functional group tolerance.

Visible-Light-Promoted Asymmetric Catalysis by Chiral Complexes of First-Row Transition Metals

Synthesis ◽  
2020 ◽  
Author(s):  
Yanjun Li ◽  
Ziqi Ye ◽  
Jiaxin Cai ◽  
Lei Gong
Keyword(s):  
Transition Metals ◽  
Visible Light ◽  
Asymmetric Catalysis ◽  
Functional Group ◽  
Short Review ◽  
Chiral Complexes ◽  
Diverse Range ◽  
Mild Conditions ◽  
Nickel Cobalt ◽  
Visible Light Driven

This short review presents an overview of visible-light-driven asymmetric catalysis by chiral complexes of first-row transition metals. The processes described here include dual catalysis by a chiral complex of copper, nickel, cobalt or chromium and an additional photoredox or energy-transfer catalyst, and bifunctional catalysis by a single chiral copper or nickel catalyst. These methods allow valuable transformations with high functional group compatibility. They provide stereoselective construction of carbon-carbon or carbon-heteroatom bonds under mild conditions, and produce a diverse range of previously unknown enantio-enriched compounds.

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