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Literature DB >> 26013998

Zinc-Catalyzed Alkyne Oxidation/C-H Functionalization: Highly Site-Selective Synthesis of Versatile Isoquinolones and β-Carbolines.

Long Li¹, Bo Zhou¹, Yong-Heng Wang², Chao Shu¹, Yi-Fei Pan¹, Xin Lu³, Long-Wu Ye⁴.

Abstract

An efficient zinc(II)-catalyzed alkyne oxidation/C-H functionalization sequence was developed, thus leading to highly site-selective synthesis of a variety of isoquinolones and β-carbolines. Importantly, in contrast to the well-established gold-catalyzed intermolecular alkyne oxidation, over-oxidation can be completely suppressed in this system and the reaction most likely proceeds by a Friedel-Crafts-type pathway. Mechanistic studies and theoretical calculations are described.

Entities: Chemical

Keywords: heterocycles; homogeneous catalysis; nitrogen oxides; synthetic methods; zinc

Mesh：

Substances：

Year: 2015 PMID： 26013998 DOI： 10.1002/anie.201502553

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

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Cited

11 in total

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Journal: ChemistryOpen Date: 2020-01-13 Impact factor: 2.911

2. Synthesis of Barbaralones and Bullvalenes Made Easy by Gold Catalysis.

Authors: Sofia Ferrer; Antonio M Echavarren
Journal: Angew Chem Int Ed Engl Date: 2016-08-19 Impact factor: 15.336

3. Divergent synthesis of N-heterocycles via controllable cyclization of azido-diynes catalyzed by copper and gold.

Authors: Wen-Bo Shen; Qing Sun; Long Li; Xin Liu; Bo Zhou; Juan-Zhu Yan; Xin Lu; Long-Wu Ye
Journal: Nat Commun Date: 2017-11-23 Impact factor: 14.919

4. Stereoselective synthesis of medium lactams enabled by metal-free hydroalkoxylation/stereospecific [1,3]-rearrangement.

Authors: Bo Zhou; Ying-Qi Zhang; Kairui Zhang; Ming-Yang Yang; Yang-Bo Chen; You Li; Qian Peng; Shou-Fei Zhu; Qi-Lin Zhou; Long-Wu Ye
Journal: Nat Commun Date: 2019-07-19 Impact factor: 14.919

5. 3-Dialkylamino-1,2,4-triazoles via Zn^II-Catalyzed Acyl Hydrazide-Dialkylcyanamide Coupling.

Authors: Sevilya N Yunusova; Dmitrii S Bolotin; Vitalii V Suslonov; Mikhail A Vovk; Peter M Tolstoy; Vadim Yu Kukushkin
Journal: ACS Omega Date: 2018-07-03

6. Synthesis of γ-substituted carbonyl compounds from DMSO-mediated oxidation of enynamides: mechanistic insights and carbon- and hetero-functionalizations.

Authors: Quynh H Nguyen; Nguyen H Nguyen; Hanbyul Kim; Seunghoon Shin
Journal: Chem Sci Date: 2019-08-12 Impact factor: 9.825

Zinc-Catalyzed Alkyne Oxidation/C-H Functionalization: Highly Site-Selective Synthesis of Versatile Isoquinolones and β-Carbolines.

Review 1. The Fascinating Chemistry of α-Haloamides.

2. Synthesis of Barbaralones and Bullvalenes Made Easy by Gold Catalysis.

3. Divergent synthesis of N-heterocycles via controllable cyclization of azido-diynes catalyzed by copper and gold.

4. Stereoselective synthesis of medium lactams enabled by metal-free hydroalkoxylation/stereospecific [1,3]-rearrangement.

5. 3-Dialkylamino-1,2,4-triazoles via Zn^II-Catalyzed Acyl Hydrazide-Dialkylcyanamide Coupling.

6. Synthesis of γ-substituted carbonyl compounds from DMSO-mediated oxidation of enynamides: mechanistic insights and carbon- and hetero-functionalizations.

7. A Zinc-Mediated Deprotective Annulation Approach to New Polycyclic Heterocycles.

8. Rh₂(ii)-catalyzed enantioselective intramolecular Büchner reaction and aromatic substitution of donor-donor carbenes.

9. Metal-free intermolecular formal cycloadditions enable an orthogonal access to nitrogen heterocycles.

10. A Gold Carbene Manifold to Prepare Fused γ-Lactams by Oxidative Cyclisation of Ynamides.