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

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).

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

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.10.316 ◽

2014 ◽

Vol 10 ◽

pp. 2981-2988 ◽

Cited By ~ 14

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.

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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

Green Chemistry ◽

10.1039/c8gc03297a ◽

2018 ◽

Vol 20 (24) ◽

pp. 5540-5549 ◽

Cited By ~ 10

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.

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

Advanced Synthesis & Catalysis ◽

10.1002/adsc.201701131 ◽

2017 ◽

Vol 360 (4) ◽

pp. 762-767 ◽

Cited By ~ 7

Author(s):

Xuan Ding ◽

Chun-Lin Dong ◽

Zhi Guan ◽

Yan-Hong He

Keyword(s):

Visible Light ◽

Tertiary Amines

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

Organic & Biomolecular Chemistry ◽

10.1039/c6ob01239f ◽

2016 ◽

Vol 14 (31) ◽

pp. 7447-7450 ◽

Cited By ~ 13

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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Visible-Light Photoredox Catalytic α-Cyanation Reactions of Tertiary Amines

Acta Chimica Sinica ◽

10.6023/a16080414 ◽

2017 ◽

Vol 75 (1) ◽

pp. 110 ◽

Cited By ~ 7

Author(s):

Quanquan Zhou ◽

Dan Liu ◽

Wenjing Xiao ◽

Liangqiu Lu

Keyword(s):

Visible Light ◽

Tertiary Amines

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Visible-Light-Promoted Asymmetric Cross-Dehydrogenative Coupling of Tertiary Amines to Ketones by Synergistic Multiple Catalysis

Angewandte Chemie ◽

10.1002/ange.201700572 ◽

2017 ◽

Vol 129 (13) ◽

pp. 3748-3752 ◽

Cited By ~ 30

Author(s):

Qi Yang ◽

Long Zhang ◽

Chen Ye ◽

Sanzhong Luo ◽

Li-Zhu Wu ◽

...

Keyword(s):

Visible Light ◽

Tertiary Amines ◽

Dehydrogenative Coupling

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Himbacine Derivatives and Synthetic Analogues

Australian Journal of Chemistry ◽

10.1071/ch9630112 ◽

1963 ◽

Vol 16 (1) ◽

pp. 112 ◽

Cited By ~ 3

Author(s):

MN Galbraith ◽

JJ Hobbs ◽

RA Massy-Westropp

Keyword(s):

Mannich Reaction ◽

Tertiary Amines ◽

Synthetic Analogues ◽

The Mannich Reaction ◽

Pharmacological Testing

A series of derivatives was prepared for pharmacological testing from himbacine and dihydrohimbacine, the latter compound obtained by von Braun degradation of dihydrohimbacine. The Mannich reaction with acetylenic acetates was used for the preparation of tertiary amines for testing. It was found that much improved yields were obtained by addition of catalytic amounts of copper(I) chloride and copper bronze to the reaction mixture.

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Efficient visible light-mediated cross-dehydrogenative coupling reactions of tertiary amines catalyzed by a polymer-immobilized iridium-based photocatalyst

Green Chemistry ◽

10.1039/c4gc00058g ◽

2014 ◽

Vol 16 (5) ◽

pp. 2438-2442 ◽

Cited By ~ 79

Author(s):

Woo-Jin Yoo ◽

Shū Kobayashi

Keyword(s):

Visible Light ◽

Heterogeneous Catalyst ◽

Coupling Reactions ◽

Tertiary Amines ◽

Visible Light Photocatalyst ◽

Dehydrogenative Coupling ◽

Polymer Supported

A polymer-supported Ir-based visible light photocatalyst was developed, and was evaluated as a heterogeneous catalyst for the aerobic phosphonylation reaction of N-aryl tetrahydroisoquinolines.

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