Literature DB >> 26031476

Sunlight-Driven Decarboxylative Alkynylation of α-Keto Acids with Bromoacetylenes by Hypervalent Iodine Reagent Catalysis: A Facile Approach to Ynones.

Hui Tan1, Hongji Li1, Wangqin Ji1, Lei Wang2,3.   

Abstract

A novel and practical decarboxylative alkynylation of α-keto acids with bromoacetylenes is catalyzed by hypervalent iodine(III) reagents when irradiation by sunlight at room temperature. The product ynones are generated in good yields. Experiments show that results obtained with blue light (λ=450-455 nm) are comparable to those obtained when using sunlight. Mechanistic studies demonstrate that the sunlight-driven decarboxylation undergoes a radical process.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  acylation; alkynes; hypervalent compounds; photochemistry; radicals

Mesh：

Substances：

Year:  2015        PMID： 26031476     DOI： 10.1002/anie.201503479

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


  13 in total

1.  Visible-light-promoted decarboxylative radical cascade cyclization to acylated benzimidazo/indolo[2,1-a]isoquinolin-6(5H)-ones in water.

Authors:  Lili Tang; Yuejun Ouyang; Kai Sun; Bing Yu
Journal:  RSC Adv       Date:  2022-07-07       Impact factor: 4.036

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.  A unified photoredox-catalysis strategy for C(sp3)-H hydroxylation and amidation using hypervalent iodine.

Authors:  Guo-Xing Li; Cristian A Morales-Rivera; Fang Gao; Yaxin Wang; Gang He; Peng Liu; Gong Chen
Journal:  Chem Sci       Date:  2017-09-04       Impact factor: 9.825

4.  Photoredox-mediated Minisci C-H alkylation of N-heteroarenes using boronic acids and hypervalent iodine.

Authors:  Guo-Xing Li; Christian A Morales-Rivera; Yaxin Wang; Fang Gao; Gang He; Peng Liu; Gong Chen
Journal:  Chem Sci       Date:  2016-07-12       Impact factor: 9.825

5.  Copper-catalyzed aminoalkynylation of alkenes with hypervalent iodine reagents.

Authors:  Kun Shen; Qiu Wang
Journal:  Chem Sci       Date:  2017-10-16       Impact factor: 9.825

6.  Investigations of alkynylbenziodoxole derivatives for radical alkynylations in photoredox catalysis.

Authors:  Yue Pan; Kunfang Jia; Yali Chen; Yiyun Chen
Journal:  Beilstein J Org Chem       Date:  2018-05-28       Impact factor: 2.883

Review 7.  Alkynylation of radicals: spotlight on the "Third Way" to transfer triple bonds.

Authors:  Franck Le Vaillant; Jérôme Waser
Journal:  Chem Sci       Date:  2019-08-13       Impact factor: 9.825

8.  Chemoenzymatic Production of Enantiocomplementary 2-Substituted 3-Hydroxycarboxylic Acids from L-α-Amino Acids.

Authors:  Mathias Pickl; Roser Marín-Valls; Jesús Joglar; Jordi Bujons; Pere Clapés
Journal:  Adv Synth Catal       Date:  2021-03-22       Impact factor: 5.837

9.  Photochemical generation of acyl and carbamoyl radicals using a nucleophilic organic catalyst: applications and mechanism thereof.

Authors:  Eduardo de Pedro Beato; Daniele Mazzarella; Matteo Balletti; Paolo Melchiorre
Journal:  Chem Sci       Date:  2020-06-04       Impact factor: 9.825

10.  Practical Synthesis of 2-Iodosobenzoic Acid (IBA) without Contamination by Hazardous 2-Iodoxybenzoic Acid (IBX) under Mild Conditions.

Authors:  Hideyasu China; Nami Kageyama; Hotaka Yatabe; Naoko Takenaga; Toshifumi Dohi
Journal:  Molecules       Date:  2021-03-27       Impact factor: 4.411
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