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Literature DB >> 23419035

A versatile C-H functionalization of tetrahydroisoquinolines catalyzed by iodine at aerobic conditions.

Jayaraman Dhineshkumar¹, Manjunath Lamani, Kaliyamoorthy Alagiri, Kandikere Ramaiah Prabhu.

Abstract

A versatile aerobic catalytic system (I(2) and O(2)/TBHP) for C-H functionalization is reported. This CDC (cross-dehydrogentive coupling) reaction is compatible with a large number of nucleophiles and is performed under ambient reaction conditions. The scope of the metal-free CDC is illustrated by synthesizing a variety of functionalized tetrahydroisoquinolines and N,N-dimethylaniline. The highlight of the method is a Friedel-Crafts reaction of phenols and indole with tertiary amines.

Entities: Chemical

Year: 2013 PMID： 23419035 DOI： 10.1021/ol4001153

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

16 in total

1. Redox-neutral α-C-H bond functionalization of secondary amines with concurrent C-P bond formation/N-alkylation.

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2. Design, synthesis and characterization of structurally dynamic cyclic N,S-acetals.

Authors: Emily K Kirkeby; Andrew G Roberts
Journal: Chem Commun (Camb) Date: 2020-07-22 Impact factor: 6.222

3. Direct phosphorylation of benzylic C-H bonds under transition metal-free conditions forming sp³C-P bonds.

Authors: Qiang Li; Chang-Qiu Zhao; Tieqiao Chen; Li-Biao Han
Journal: RSC Adv Date: 2022-06-24 Impact factor: 4.036

4. Redox-neutral α-arylation of amines.

Authors: Weijie Chen; Richard G Wilde; Daniel Seidel
Journal: Org Lett Date: 2013-12-13 Impact factor: 6.005

5. Bioinspired aerobic oxidation of secondary amines and nitrogen heterocycles with a bifunctional quinone catalyst.

Authors: Alison E Wendlandt; Shannon S Stahl
Journal: J Am Chem Soc Date: 2013-12-18 Impact factor: 15.419

6. Metal-free C(sp(3))-H functionalization: oxidative carbo-oxygenation of α-diazo carbonyls via radical dediazotization.

Authors: Nan-Nan Wang; Wen-Juan Hao; Tian-Shu Zhang; Guigen Li; Ya-Nan Wu; Shu-Jiang Tu; Bo Jiang
Journal: Chem Commun (Camb) Date: 2016-03-21 Impact factor: 6.222

A versatile C-H functionalization of tetrahydroisoquinolines catalyzed by iodine at aerobic conditions.

1. Redox-neutral α-C-H bond functionalization of secondary amines with concurrent C-P bond formation/N-alkylation.

2. Design, synthesis and characterization of structurally dynamic cyclic N,S-acetals.

3. Direct phosphorylation of benzylic C-H bonds under transition metal-free conditions forming sp³C-P bonds.

4. Redox-neutral α-arylation of amines.

5. Bioinspired aerobic oxidation of secondary amines and nitrogen heterocycles with a bifunctional quinone catalyst.

6. Metal-free C(sp(3))-H functionalization: oxidative carbo-oxygenation of α-diazo carbonyls via radical dediazotization.

7. Synthesis of (±)-Tetrabenazine by Visible Light Photoredox Catalysis.

8. Dual C-H functionalization of N-aryl amines: synthesis of polycyclic amines via an oxidative Povarov approach.

9. The redox-Mannich reaction.

10. Regiodivergent synthesis of pyrazino-indolines vs. triazocines via α-imino carbenes addition to imidazolidines.