Late-Stage Functionalization of Arylacetic Acids by Photoredox-Catalyzed Decarboxylative Carbon-Heteroatom Bond Formation

2018 ◽  
Vol 24 (37) ◽  
pp. 9254-9258 ◽  
Author(s):  
Yota Sakakibara ◽  
Eri Ito ◽  
Tomohiro Fukushima ◽  
Kei Murakami ◽  
Kenichiro Itami
Keyword(s):  
Late Stage ◽  
Bond Formation ◽  
Arylacetic Acids

scholarly journals Kinetic resolution of indolines by asymmetric hydroxylamine formation

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Gang Wang ◽  
Ran Lu ◽  
Chuangchuang He ◽  
Lei Liu
Keyword(s):  
Hydrogen Peroxide ◽  
Chemical Synthesis ◽  
Late Stage ◽  
Kinetic Resolution ◽  
High Efficiency ◽  
Bond Formation ◽  
Bioactive Molecules ◽  
Environmentally Benign ◽  
Secondary Amines

AbstractCatalytic kinetic resolution of amines represents a longstanding challenge in chemical synthesis. Here, we described a kinetic resolution of secondary amines through oxygenation to produce enantiopure hydroxylamines involving N–O bond formation. The economic and practical titanium-catalyzed asymmetric oxygenation with environmentally benign hydrogen peroxide as oxidant is applicable to a range of racemic indolines with multiple stereocenters and diverse substituent patterns in high efficiency with efficient chemoselectivity and enantio-discrimination. Late-stage asymmetric oxygenation of bioactive molecules that are otherwise difficult to synthesize was also explored.

One-Pot Access to 4-Aryl-2-arylacetoxynaphthalenes via Benz­annulation of Oxygenated Arylacetic Acids and Alkyl Aryl Ketones

Synthesis ◽  
2020 ◽  
Vol 52 (07) ◽  
pp. 1035-1046 ◽  
Author(s):  
Meng-Yang Chang ◽  
Shin-Mei Chen ◽  
Yu-Ting Hsiao
Keyword(s):  
Bond Formation ◽  
Trifluoroacetic Anhydride ◽  
Ring Closure ◽  
One Pot ◽  
Alkyl Aryl ◽  
Highly Effective ◽  
Aryl Ketones ◽  
Arylacetic Acids ◽  
Plausible Mechanism

Trifluoroacetic anhydride mediated one-pot intermolecular formal (4+2) benzannulation of oxygenated arylacetic acids with alkyl aryl ketones provides 4-aryl-2-arylacetoxynaphthalenes in moderate to good yields in the presence of H3PO4 in an open-vessel in a straightforward procedure. A plausible mechanism is proposed and discussed. This protocol provides a highly effective ring-closure via two carbon–carbon (C–C) and one carbon–oxygen (C–O) bond-formation events.

Metal-Free Insertion of Sulfoxonium Ylides into Arylamines in Water

Synthesis ◽  
2020 ◽  
Author(s):  
Mei Guan ◽  
Yong Wu ◽  
Hua He ◽  
Kaichuan Yan ◽  
Jianglian Li ◽  
...  
Keyword(s):  
Organic Solvents ◽  
Bioactive Compounds ◽  
Late Stage ◽  
Bond Formation ◽  
Metal Catalysts ◽  
Significant Development ◽  
Metal Free ◽  
Water As Solvent ◽  
Mild Temperature

Carbenoid-based N–H insertions have undergone significant development with respect to C–N bond formation in recent years. However, the existing methods suffer from unstable starting materials, expensive metal catalysts and organic solvents. Herein, insertion of sulfoxonium ylides into arylamines under metal-free conditions has been developed. The method employs water as solvent at mild temperature and is amenable to the late-stage modification of structurally complex bioactive compounds.

scholarly journals Nickel-Catalyzed Thiolation of Aryl Nitriles

2021 ◽  
Author(s):  
Tristan Delcaillau ◽  
Bill Morandi
Keyword(s):  
Late Stage ◽  
Functional Group ◽  
Bond Activation ◽  
Bond Formation ◽  
Aryl Nitriles

<div>A nickel-catalyzed thiolation of aryl nitriles has been developed to access functionalized aryl thioethers. The ligand dcype (1,2 Bis(dicyclohexylphosphino)ethane) as well as the base KOtBu (potassium tert-butoxide) are essential to achieve this transformation. This scalable and practical process involves both a C–C bond activation and a C–S bond formation. Furthermore, this reaction shows a high functional-group tolerance and enables the late-stage functionalization of important molecules.</div>

scholarly journals Site-Selective Alkoxylation of Benzylic C–H Bonds via Photoredox Catalysis

2019 ◽  
Author(s):  
Byung Joo Lee ◽  
kimberly deglopper ◽  
Tehshik Yoon
Keyword(s):  
Late Stage ◽  
Functional Group ◽  
Bond Formation ◽  
Bioactive Molecules ◽  
Site Selectivity ◽  
Wide Range ◽  
High Site ◽  
Alkoxy Groups ◽  
Site Selective ◽  
Mediated Oxidation

<div> <div> <div> <p>There are relatively few methods that accom- plish the selective alkoxylation of sp3-hybridized C–H bonds, particularly in comparison to the numerous analogous strate- gies for C–N and C–C bond formation. We report a photo- catalytic protocol for the functionalization of benzylic C–H bonds with a wide range of readily available oxygen nucleo- philes. Our strategy merges the photoredox activation of arenes with copper(II)-mediated oxidation of the resulting benzylic radicals, which enables the introduction of benzylic C–O bonds with high site selectivity, chemoselectivity, and functional group tolerance. This method enables the late- stage introduction of complex alkoxy groups into bioactive molecules, providing a practical new tool with potential appli- cations in synthesis and medicinal chemistry. </p> </div> </div> </div>

scholarly journals Site-Selective Alkoxylation of Benzylic C–H Bonds via Photoredox Catalysis

2019 ◽  
Author(s):  
Byung Joo Lee ◽  
kimberly deglopper ◽  
Tehshik Yoon
Keyword(s):  
Late Stage ◽  
Functional Group ◽  
Bond Formation ◽  
Bioactive Molecules ◽  
Site Selectivity ◽  
Wide Range ◽  
High Site ◽  
Alkoxy Groups ◽  
Site Selective ◽  
Mediated Oxidation

<div> <div> <div> <p>There are relatively few methods that accom- plish the selective alkoxylation of sp3-hybridized C–H bonds, particularly in comparison to the numerous analogous strate- gies for C–N and C–C bond formation. We report a photo- catalytic protocol for the functionalization of benzylic C–H bonds with a wide range of readily available oxygen nucleo- philes. Our strategy merges the photoredox activation of arenes with copper(II)-mediated oxidation of the resulting benzylic radicals, which enables the introduction of benzylic C–O bonds with high site selectivity, chemoselectivity, and functional group tolerance. This method enables the late- stage introduction of complex alkoxy groups into bioactive molecules, providing a practical new tool with potential appli- cations in synthesis and medicinal chemistry. </p> </div> </div> </div>

scholarly journals Site-Selective Alkoxylation of Benzylic C–H Bonds via Photoredox Catalysis

2019 ◽  
Author(s):  
Byung Joo Lee ◽  
kimberly deglopper ◽  
Tehshik Yoon
Keyword(s):  
Late Stage ◽  
Functional Group ◽  
Bond Formation ◽  
Bioactive Molecules ◽  
Site Selectivity ◽  
Wide Range ◽  
High Site ◽  
Alkoxy Groups ◽  
Site Selective ◽  
Mediated Oxidation

<div> <div> <div> <p>There are relatively few methods that accom- plish the selective alkoxylation of sp3-hybridized C–H bonds, particularly in comparison to the numerous analogous strate- gies for C–N and C–C bond formation. We report a photo- catalytic protocol for the functionalization of benzylic C–H bonds with a wide range of readily available oxygen nucleo- philes. Our strategy merges the photoredox activation of arenes with copper(II)-mediated oxidation of the resulting benzylic radicals, which enables the introduction of benzylic C–O bonds with high site selectivity, chemoselectivity, and functional group tolerance. This method enables the late- stage introduction of complex alkoxy groups into bioactive molecules, providing a practical new tool with potential appli- cations in synthesis and medicinal chemistry. </p> </div> </div> </div>

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