scholarly journals Visible light-enabled radical Mannich reaction via sp3 C-H bond functionalization of tertiary amines

2021 ◽  
Author(s):  
NGUYEN HUONG QUYNH ◽  
Seunghoon Shin
Keyword(s):  
Visible Light ◽  
Mannich Reaction ◽  
Tertiary Amines ◽  
Bond Functionalization

Visible light catalyzed Mannich reaction between tert-amines and silyl diazoenolates

2017 ◽  
Vol 15 (35) ◽  
pp. 7369-7373 ◽  
Author(s):  
Mukund M. D. Pramanik ◽  
Savita B. Nagode ◽  
Ruchir Kant ◽  
Namrata Rastogi
Keyword(s):  
Visible Light ◽  
Mannich Reaction ◽  
Tertiary Amines

The present work documents the α-C–H functionalization of tertiary amines via the visible light catalyzed Mannich reaction with silyl diazoenolates.

scholarly journals Visible Light Promoted Photoredox C(sp3)–H Bond Functionalization of Tetrahydroisoquinolines in Flow

2021 ◽  
Author(s):  
Ana Filipović ◽  
Zdravko Dzambaski ◽  
Dana Vasiljevic-Radovic ◽  
Bojan Bondžić
Keyword(s):  
Visible Light ◽  
Mannich Reaction ◽  
Photoredox Catalysis ◽  
Bond Functionalization ◽  
Wide Range

A merger of organocatalysis and visible light photoredox catalysis performed in flow allowed access to a wide range of functionalized N-Aryl-substituted tetrahydoisoquinolines (THIQs) in a formal C-H oxidation/Mannich reaction. Strecker...

Catalyst-Free [2,3]-Sigmatropic Rearrangement Reactions of Photochemically Generated Ammonium Ylides

Synthesis ◽  
2019 ◽  
Vol 51 (23) ◽  
pp. 4348-4358 ◽  
Author(s):  
Fang Li ◽  
Feifei He ◽  
Rene M. Koenigs
Keyword(s):  
Visible Light ◽  
Sigmatropic Rearrangement ◽  
Tertiary Amines ◽  
Amino Esters ◽  
Catalyst Free ◽  
Rearrangement Reaction ◽  
Rearrangement Reactions ◽  
Free Ammonium

The rearrangement reaction of ammonium ylides furnishes valuable α,α-disubstituted amino esters. In this work, we describe the visible-light photolysis reaction of aryldiazoacetates in the presence of tertiary amines that react via a free ammonium ylide in a sigmatropic rearrangement reaction to provide amino esters in moderate to very good yields (33 examples, up to 97% yield).

Visible Light-Induced C−H Bond Functionalization: A Critical Review

2018 ◽  
Vol 360 (24) ◽  
pp. 4652-4698 ◽  
Author(s):  
Lekkala Revathi ◽  
Lekkala Ravindar ◽  
Wan-Yin Fang ◽  
K. P. Rakesh ◽  
Hua-Li Qin
Keyword(s):  
Visible Light ◽  
Critical Review ◽  
Bond Functionalization

scholarly journals One-pot functionalisation of N-substituted tetrahydroisoquinolines by photooxidation and tunable organometallic trapping of iminium intermediates

2014 ◽  
Vol 10 ◽  
pp. 2981-2988 ◽  
Author(s):  
Joshua P Barham ◽  
Matthew P John ◽  
John A Murphy
Keyword(s):  
Visible Light ◽  
Tertiary Amines ◽  
One Pot ◽  
Carbon Nucleophiles ◽  
Iminium Salts ◽  
Iminium Ions ◽  
Nucleophilic Trapping ◽  
Limited Scope

Nucleophilic trapping of iminium salts generated via oxidative functionalisation of tertiary amines is well established with stabilised carbon nucleophiles. The few reports of organometallic additions have limited scope of substrate and organometallic nucleophile. We report a novel, one-pot methodology that functionalises N-substituted tetrahydroisoquinolines by visible light-assisted photooxidation, followed by trapping of the resultant iminium ions with organometallic nucleophiles. This affords 1,2-disubstituted tetrahydroisoquinolines in moderate to excellent yields.

scholarly journals TiO2 Photocatalyzed C–H Bond Transformation for C–C Coupling Reactions

Catalysts ◽  
2018 ◽  
Vol 8 (9) ◽  
pp. 355 ◽  
Author(s):  
Yi Wang ◽  
Anan Liu ◽  
Dongge Ma ◽  
Shuhong Li ◽  
Chichong Lu ◽  
...  
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Visible Light Irradiation ◽  
Transition Metal Catalysis ◽  
Light Irradiation ◽  
Coupling Reactions ◽  
Metal Catalysis ◽  
Bond Functionalization ◽  
Tio2 Photocatalysis ◽  
Mild Conditions

Fulfilling the direct inert C–H bond functionalization of raw materials that are earth-abundant and commercially available for the synthesis of diverse targeted organic compounds is very desirable and its implementation would mean a great reduction of the synthetic steps required for substrate prefunctionalization such as halogenation, borylation, and metalation. Successful C–H bond functionalization mainly resorts to homogeneous transition-metal catalysis, albeit sometimes suffering from poor catalyst reusability, nontrivial separation, and severe biotoxicity. TiO2 photocatalysis displays multifaceted advantages, such as strong oxidizing ability, high chemical stability and photostability, excellent reusability, and low biotoxicity. The chemical reactions started and delivered by TiO2 photocatalysts are well known to be widely used in photocatalytic water-splitting, organic pollutant degradation, and dye-sensitized solar cells. Recently, TiO2 photocatalysis has been demonstrated to possess the unanticipated ability to trigger the transformation of inert C–H bonds for C–C, C–N, C–O, and C–X bond formation under ultraviolet light, sunlight, and even visible-light irradiation at room temperature. A few important organic products, traditionally synthesized in harsh reaction conditions and with specially functionalized group substrates, are continuously reported to be realized by TiO2 photocatalysis with simple starting materials under very mild conditions. This prominent advantage—the capability of utilizing cheap and readily available compounds for highly selective synthesis without prefunctionalized reactants such as organic halides, boronates, silanes, etc.—is attributed to the overwhelmingly powerful photo-induced hole reactivity of TiO2 photocatalysis, which does not require an elevated reaction temperature as in conventional transition-metal catalysis. Such a reaction mechanism, under typically mild conditions, is apparently different from traditional transition-metal catalysis and beyond our insights into the driving forces that transform the C–H bond for C–C bond coupling reactions. This review gives a summary of the recent progress of TiO2 photocatalytic C–H bond activation for C–C coupling reactions and discusses some model examples, especially under visible-light irradiation.

Visible light-mediated organophotocatalyzed C–H bond functionalization reactions

2019 ◽  
Vol 17 (22) ◽  
pp. 5475-5489 ◽  
Author(s):  
Mustafa Uygur ◽  
Olga García Mancheño
Keyword(s):  
Visible Light ◽  
Bond Functionalization ◽  
Recent Developments ◽  
A Current

This review provides a current overview of the recent developments in the visible light mediated organophotocatalyzed C–H bond functionalization methodologies.

Solvent-free and room temperature visible light-induced C–H activation: CdS as a highly efficient photo-induced reusable nano-catalyst for the C–H functionalization cyclization of t-amines and C–C double and triple bonds

2018 ◽  
Vol 20 (24) ◽  
pp. 5540-5549 ◽  
Author(s):  
Somayeh Firoozi ◽  
Mona Hosseini-Sarvari ◽  
Mehdi Koohgard
Keyword(s):  
Visible Light ◽  
Room Temperature ◽  
Solvent Free ◽  
Tertiary Amines ◽  
Triple Bonds ◽  
Highly Efficient ◽  
Nano Catalyst

Nano-sized CdS was successfully prepared, fully characterized and applied as a highly efficient reusable photocatalyst for the condensation of tertiary amines with double and triple bonds via a C–H activation approach.

Visible-Light-Promoted Alkylation of Indoles with Tertiary Amines by the Oxidation of a sp 3 C-H Bond

2017 ◽  
Vol 360 (4) ◽  
pp. 762-767 ◽  
Author(s):  
Xuan Ding ◽  
Chun-Lin Dong ◽  
Zhi Guan ◽  
Yan-Hong He
Keyword(s):  
Visible Light ◽  
Tertiary Amines

Brønsted acid cocatalysis in photocatalytic intramolecular coupling of tertiary amines: efficient synthesis of 2-arylindols

2016 ◽  
Vol 14 (31) ◽  
pp. 7447-7450 ◽  
Author(s):  
Xiaoqian Yuan ◽  
Xinxin Wu ◽  
Shupeng Dong ◽  
Guibing Wu ◽  
Jinxing Ye
Keyword(s):  
Visible Light ◽  
Visible Light Irradiation ◽  
Room Temperature ◽  
Coupling Reaction ◽  
Bronsted Acid ◽  
Tertiary Amines ◽  
Brønsted Acid ◽  
Efficient Synthesis ◽  
Unsaturated Ketones ◽  
Brönsted Acid

We report herein a highly efficient intramolecular coupling reaction of tertiary amines and ketones (α,β-unsaturated ketones) by using a Brønsted acid as a cocatalyst, affording 2-arylindols in good to excellent yields (up to 92%) under visible light irradiation at room temperature.

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