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Literature DB >> 25495248

Preparation of 3-Acyl-4-arylcoumarins via Metal-Free Tandem Oxidative Acylation/Cyclization between Alkynoates with Aldehydes.

Xia Mi¹, Chenyang Wang¹, Mengmeng Huang¹, Yusheng Wu², Yangjie Wu¹.

Abstract

A new and efficient metal-free tandem acylation/cyclization of alkynoates with aldehydes was developed for the synthesis of 3-acyl-4-arylcoumarins. The reaction was achieved by the addition of acyl radical to alkynes and a C-H bond functionalization to form two new C-C bonds simultaneously.

Entities: Chemical

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Year: 2014 PMID： 25495248 DOI： 10.1021/jo502220b

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

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Cited

9 in total

Review 1. Alkynoates as Versatile and Powerful Chemical Tools for the Rapid Assembly of Diverse Heterocycles under Transition-Metal Catalysis: Recent Developments and Challenges.

Authors: Imtiaz Khan; Aliya Ibrar; Sumera Zaib
Journal: Top Curr Chem (Cham) Date: 2021-01-05

2. Acyl Radical Chemistry via Visible-Light Photoredox Catalysis.

Authors: Arghya Banerjee; Zhen Lei; Ming-Yu Ngai
Journal: Synthesis (Stuttg) Date: 2018-12-12 Impact factor: 3.157

3. One-pot preparation of 4-aryl-3-bromocoumarins from 4-aryl-2-propynoic acids with diaryliodonium salts, TBAB, and Na₂S₂O₈.

Authors: Teppei Sasaki; Katsuhiko Moriyama; Hideo Togo
Journal: Beilstein J Org Chem Date: 2018-02-05 Impact factor: 2.883

4. Copper-catalyzed cascade annulation of unsaturated α-bromocarbonyls with enynals: a facile access to ketones from aldehydes.

Authors: Chao Che; Qianwen Huang; Hanliang Zheng; Gangguo Zhu
Journal: Chem Sci Date: 2016-03-04 Impact factor: 9.825

Preparation of 3-Acyl-4-arylcoumarins via Metal-Free Tandem Oxidative Acylation/Cyclization between Alkynoates with Aldehydes.

Review 1. Alkynoates as Versatile and Powerful Chemical Tools for the Rapid Assembly of Diverse Heterocycles under Transition-Metal Catalysis: Recent Developments and Challenges.

2. Acyl Radical Chemistry via Visible-Light Photoredox Catalysis.

3. One-pot preparation of 4-aryl-3-bromocoumarins from 4-aryl-2-propynoic acids with diaryliodonium salts, TBAB, and Na₂S₂O₈.

4. Copper-catalyzed cascade annulation of unsaturated α-bromocarbonyls with enynals: a facile access to ketones from aldehydes.

5. Synthesis of 2H-Chromenones from Salicylaldehydes and Arylacetonitriles.

6. A computational study for the reaction mechanism of metal-free cyanomethylation of aryl alkynoates with acetonitrile.

7. ZnBr₂/Oxone-mediated ipso-cyclization of N-(3-phenylprop-2-yn-1-yl)aniline.

Review 8. Recent Advances in the Synthesis of Coumarin Derivatives from Different Starting Materials.

9. Coumarins by Direct Annulation: β-Borylacrylates as Ambiphilic C₃ -Synthons.