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Literature DB >> 26791886

Cobalt-Catalyzed Oxidative Annulation of Nitrogen-Containing Arenes with Alkynes: An Atom-Economical Route to Heterocyclic Quaternary Ammonium Salts.

Sekar Prakash¹, Krishnamoorthy Muralirajan¹, Chien-Hong Cheng².

Abstract

Four cobalt-catalyzed oxidative annulation reactions of nitrogen-containing arenes with alkynes proceeds by C-H activation, thus leading to biologically useful quaternary ammonium salts, including pyridoisoquinolinium, cinnolinium, isoquinolinium, and quinolizinium salts, in high yields. The results are comparable to those reactions catalyzed by rhodium and ruthenium complexes. The transformation of the salts into various N-heterocycles has also been demonstrated.

Entities: Chemical Disease

Keywords: C−H activation; alkynes; annulations; cobalt; heterocycles

Year: 2016 PMID： 26791886 DOI： 10.1002/anie.201509316

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

7 in total

1. Highly Stereoselective Cobalt(III)-Catalyzed Three-Component C-H Bond Addition Cascade.

Authors: Jeffrey A Boerth; Joshua R Hummel; Jonathan A Ellman
Journal: Angew Chem Int Ed Engl Date: 2016-06-15 Impact factor: 15.336

2. Rh(iii)-catalyzed synthesis of tetracyclic isoquinolinium salts via C-H activation and [4+2] annulation of 1-phenyl-3,4-dihydroisoquinolines and alkynes in ethanol.

Authors: Xinxin Dang; Yu He; Yingtian Liu; Xuehong Chen; Jun-Long Li; Xian-Li Zhou; Hezhong Jiang; Jiahong Li
Journal: RSC Adv Date: 2018-08-24 Impact factor: 4.036

3. Rhodium-Catalyzed [4 + 1] Cyclization via C-H Activation for the Synthesis of Divergent Heterocycles Bearing a Quaternary Carbon.

Authors: Xiaowei Wu; Haitao Ji
Journal: J Org Chem Date: 2018-04-09 Impact factor: 4.354

Review 4. A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.

Authors: Carlo Sambiagio; David Schönbauer; Remi Blieck; Toan Dao-Huy; Gerit Pototschnig; Patricia Schaaf; Thomas Wiesinger; Muhammad Farooq Zia; Joanna Wencel-Delord; Tatiana Besset; Bert U W Maes; Michael Schnürch
Journal: Chem Soc Rev Date: 2018-08-28 Impact factor: 54.564

Cobalt-Catalyzed Oxidative Annulation of Nitrogen-Containing Arenes with Alkynes: An Atom-Economical Route to Heterocyclic Quaternary Ammonium Salts.

1. Highly Stereoselective Cobalt(III)-Catalyzed Three-Component C-H Bond Addition Cascade.

2. Rh(iii)-catalyzed synthesis of tetracyclic isoquinolinium salts via C-H activation and [4+2] annulation of 1-phenyl-3,4-dihydroisoquinolines and alkynes in ethanol.

3. Rhodium-Catalyzed [4 + 1] Cyclization via C-H Activation for the Synthesis of Divergent Heterocycles Bearing a Quaternary Carbon.

Review 4. A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.

5. Cobalt-catalysed C-H carbonylative cyclisation of aliphatic amides.

6. Cobalt catalyzed carbonylation of unactivated C(sp³)-H bonds.

7. Cobalt(iii)-catalyzed site-selective C-H amidation of pyridones and isoquinolones.

Cobalt-Catalyzed Oxidative Annulation of Nitrogen-Containing Arenes with Alkynes: An Atom-Economical Route to Heterocyclic Quaternary Ammonium Salts.

1. Highly Stereoselective Cobalt(III)-Catalyzed Three-Component C-H Bond Addition Cascade.

2. Rh(iii)-catalyzed synthesis of tetracyclic isoquinolinium salts via C-H activation and [4+2] annulation of 1-phenyl-3,4-dihydroisoquinolines and alkynes in ethanol.

3. Rhodium-Catalyzed [4 + 1] Cyclization via C-H Activation for the Synthesis of Divergent Heterocycles Bearing a Quaternary Carbon.

Review 4. A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.

5. Cobalt-catalysed C-H carbonylative cyclisation of aliphatic amides.

6. Cobalt catalyzed carbonylation of unactivated C(sp3)-H bonds.

7. Cobalt(iii)-catalyzed site-selective C-H amidation of pyridones and isoquinolones.

6. Cobalt catalyzed carbonylation of unactivated C(sp³)-H bonds.