Visible-Light-Triggered Decarboxylative Alkylation of 8-Acylaminoquinoline with N-Hydroxyphthalimide Ester

Synlett ◽  
2020 ◽  
Vol 31 (07) ◽  
pp. 677-682 ◽  
Author(s):  
Bin Sun ◽  
Deyu Li ◽  
Xiaohui Zhuang ◽  
Rui Zhu ◽  
Aertuke Aisha ◽  
...  
Keyword(s):  
Visible Light ◽  
Functional Groups ◽  
Efficient Approach ◽  
Radical Coupling ◽  
Mild Conditions ◽  
Highly Efficient ◽  
Wide Range ◽  
Reaction Proceeds ◽  
Operational Simplicity

A facile protocol for visible-light-induced decarboxylative radical coupling of NHP esters with 8-aminoquinoline amides is reported, affording a highly efficient approach to synthesize a variety of 2-alkylated or 2,4-dialkylated 8-aminoquinoline derivatives. The reaction proceeds smoothly without adding any ligand, and provides the corresponding products containing a wide range of functional groups in moderate to excellent yields. This reaction uses readily available starting materials, and proceeds under mild conditions and with operational simplicity.

Iron-Catalyzed Regioselective Decarboxylative Alkylation of Coumarins and Chromones with Alkyl Diacyl Peroxides

Synlett ◽  
2019 ◽  
Vol 30 (13) ◽  
pp. 1585-1591 ◽  
Author(s):  
Can Jin ◽  
Xun Zhang ◽  
Bin Sun ◽  
Zhiyang Yan ◽  
Tengwei Xu
Keyword(s):  
Functional Groups ◽  
Wide Scope ◽  
Efficient Approach ◽  
Radical Coupling ◽  
Highly Efficient ◽  
Operational Simplicity

A facile iron-catalyzed decarboxylative radical coupling of alkyl diacyl peroxides with coumarins or chromones has been developed, affording a highly efficient approach to synthesize a variety of α-alkylated coumarins and β-alkylated chromones. The reaction proceeded smoothly without adding any ligand or additive and provided the corresponding products containing a wide scope of functional groups in moderate to excellent yields. This protocol was highlighted by its high regioselectivity, readily available starting materials, and operational simplicity.

Visible-Light-Promoted Radical Cyclization of N-Arylvinylsulfonamides: Synthesis of CF3/CHF2/CH2CF3-Containing 1,3-Dihydrobenzo[c]isothiazole 2,2-Dioxide Derivatives

Synthesis ◽  
2021 ◽  
Author(s):  
Devaiah Vytla ◽  
Kumargurubaran Kaliyaperumal ◽  
Rajeswari Velayuthaperumal ◽  
Parinita Shaw ◽  
Raj Gautam ◽  
...  
Keyword(s):  
Visible Light ◽  
Radical Cyclization ◽  
Mild Conditions ◽  
Highly Efficient ◽  
Reaction Proceeds ◽  
High Yields

AbstractA photocatalyzed and highly efficient trifluoromethylation of N-arylvinylsulfonamides using commercially available CF3SO2Cl as the trifluoromethyl radical source under blue LEDs is reported. The reaction proceeds through radical cyclization under mild conditions. An investigation of the substrate scope is performed to establish a general, synthetically useful protocol for the synthesis of novel trifluoromethylated 1,3-dihydrobenzo[c]isothiazole 2,2-dioxides in moderate to high yields. This method is also successfully applied for the synthesis of difluoromethylated and trifluoroethylated 1,3-dihydrobenzo[c]isothiazole 2,2-dioxides in good to excellent yields.

scholarly journals Asymmetric Synthesis of Tetrahydroisoquinoline Derivatives through 1,3-Dipolar Cycloaddition of C,N-Cyclic Azomethine Imines with Allyl Alkyl Ketones

Molecules ◽  
2021 ◽  
Vol 26 (10) ◽  
pp. 2969
Author(s):  
Guipeng Feng ◽  
Guoyang Ma ◽  
Wenyan Chen ◽  
Shaohong Xu ◽  
Kaikai Wang ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Functional Groups ◽  
Absolute Configuration ◽  
Dipolar Cycloaddition ◽  
Quantum Electronic ◽  
Mild Conditions ◽  
Spectrum Method ◽  
Wide Range ◽  
Reaction Proceeds ◽  
Azomethine Imines

[3 + 2] A 1,3-Dipolar cycloaddition of C,N-cyclic azomethine imines with allyl alkyl ketones has been achieved. The reaction proceeds under mild conditions and tolerates a wide range of functional groups. An array of tetrahydroisoquinoline derivatives is generally constructed with good diastereoselectivities and enantioselectivities (up to >25:1 dr, >95% ee). Moreover, the absolute configuration of the product was previously determined by using the quantum electronic circular dichroism calculation and ECD spectrum method.

Synthesis of 1,3,4-Oxadiazoles by Iodine-mediated Oxidative Cyclization of Methyl Ketones with 4-Phenylsemicarbazide

Synlett ◽  
2021 ◽  
Author(s):  
Shanshan Zhang ◽  
Chuang Liu ◽  
Xiaojun Wu ◽  
Wen Li ◽  
He Li ◽  
...  
Keyword(s):  
Functional Groups ◽  
Oxidative Cyclization ◽  
Methyl Ketones ◽  
One Pot ◽  
Mild Conditions ◽  
Wide Range ◽  
Reaction Proceeds ◽  
Aryl Methyl

An efficient one-pot method to access 5-amino-2-benzoyl-1,3,4-oxadiazoles via I2/DMSO promoted oxidative cyclization of 4-phenylsemicarbazide with (het)aryl methyl ketones under mild conditions was developed. This reaction proceeds smoothly with a wide range of methyl ketones containing different functional groups to give the corresponding products in moderate yields under mild conditions.

Oxidation of 4-Aryl-1,1,1-trifluorobut-2-en-2-yl Trifluoro­methanesulfonates by 4-Picoline-N-Oxide: A Novel Approach to β-Trifluoromethyl-α,β-enones

Synthesis ◽  
2020 ◽  
Vol 52 (08) ◽  
pp. 1203-1210 ◽  
Author(s):  
Dong Li ◽  
Shujun Lv ◽  
Jingping Qu ◽  
Yuhan Zhou
Keyword(s):  
Functional Groups ◽  
Efficient Approach ◽  
Novel Approach ◽  
Wide Range ◽  
Reaction Proceeds

An efficient approach to β-trifluoromethyl-α,β-enones via oxidation of 4-aryl-1,1,1-trifluorobut-2-en-2-yl trifluoromethanesulfonates is described. The reaction proceeds smoothly under mild and metal­-free conditions and tolerates a wide range of functional groups. Various β-trifluoromethyl-α,β-enones were obtained in moderate to good yields.

Visible Light-Promoted Catalytic Ring-Opening Isomerization of 1,2-Disubstituted Cyclopropanols to Linear Ketones

2019 ◽  
Author(s):  
Marharyta V. Laktsevich-Iskryk ◽  
Nastassia A. Varabyeva ◽  
Volha V. Kazlova ◽  
Vladimir N. Zhabinskii ◽  
Vladimir A. Khripach ◽  
...  
Keyword(s):  
Visible Light ◽  
Functional Groups ◽  
Ring Opening ◽  
Radical Intermediates ◽  
Reaction Proceeds

In this article, we report a photocatalytic protocol for the isomerization of 1,2-disubstituted cyclopropanols to linear ketones. The reaction proceeds <i>via</i> radical intermediates and tolerates various functional groups.

Visible Light-Promoted Catalytic Ring-Opening Isomerization of 1,2-Disubstituted Cyclopropanols to Linear Ketones

2019 ◽  
Author(s):  
Marharyta V. Laktsevich-Iskryk ◽  
Nastassia A. Varabyeva ◽  
Volha V. Kazlova ◽  
Vladimir N. Zhabinskii ◽  
Vladimir A. Khripach ◽  
...  
Keyword(s):  
Visible Light ◽  
Functional Groups ◽  
Ring Opening ◽  
Radical Intermediates ◽  
Reaction Proceeds

In this article, we report a photocatalytic protocol for the isomerization of 1,2-disubstituted cyclopropanols to linear ketones. The reaction proceeds <i>via</i> radical intermediates and tolerates various functional groups.

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

Visible light-photocatalysed carbazole synthesis via a formal (4+2) cycloaddition of indole-derived bromides and alkynes

2016 ◽  
Vol 52 (29) ◽  
pp. 5128-5131 ◽  
Author(s):  
Zhi-Guang Yuan ◽  
Qiang Wang ◽  
Ang Zheng ◽  
Kai Zhang ◽  
Liang-Qiu Lu ◽  
...  
Keyword(s):  
Visible Light ◽  
Mild Conditions ◽  
Wide Range

We have developed an unprecedented route to carbazole by a visible light-photocatalysed formal (4+2) cycloaddition of indole-derived bromides and alkynes. Using this method, a wide range of highly functionalised carbazoles were produced in good yields under mild conditions.

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.

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