Literature DB >> 28929553

Alkynylation of Csp2 (O)-H Bonds Enabled by Photoredox-Mediated Hydrogen-Atom Transfer.

Satobhisha Mukherjee1, R Aleyda Garza-Sanchez1, Adrian Tlahuext-Aca1, Frank Glorius1.   

Abstract

The development of new hydrogen-atom transfer (HAT) strategies within the framework of photoredox catalysis is highly appealing for its power to activate a desired C-H bond in the substrate leading to its selective functionalization. Reported here is the first photoredox-mediated hydrogen-atom transfer method for the efficient synthesis of ynones, ynamides, and ynoates with high regio- and chemoselectivity by direct functionalization of Csp2 (O)-H bonds. The broad synthetic application of this method has been demonstrated by the selective functionalization of C(O)-H bonds within complex molecular scaffolds.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−H activation; carbonyl radicals; hydrogen-atom transfer; hypervalent compounds; photocatalysis

Year:  2017        PMID: 28929553     DOI: 10.1002/anie.201708037

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


  14 in total

Review 1.  Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.

Authors:  Philip R D Murray; James H Cox; Nicholas D Chiappini; Casey B Roos; Elizabeth A McLoughlin; Benjamin G Hejna; Suong T Nguyen; Hunter H Ripberger; Jacob M Ganley; Elaine Tsui; Nick Y Shin; Brian Koronkiewicz; Guanqi Qiu; Robert R Knowles
Journal:  Chem Rev       Date:  2021-11-23       Impact factor: 60.622

2.  Photoinduced inverse Sonogashira coupling reaction.

Authors:  Lizhu Zhang; Cunbo Wei; Jiawen Wu; Dan Liu; Yinchao Yao; Zhuo Chen; Jianxun Liu; Chang-Jiang Yao; Dinghua Li; Rongjie Yang; Zhonghua Xia
Journal:  Chem Sci       Date:  2022-05-30       Impact factor: 9.969

3.  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

4.  Combined Photoredox and Carbene Catalysis for the Synthesis of Ketones from Carboxylic Acids.

Authors:  Anna V Davies; Keegan P Fitzpatrick; Rick C Betori; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2020-03-24       Impact factor: 15.336

Review 5.  Photoredox-Catalyzed C-H Functionalization Reactions.

Authors:  Natalie Holmberg-Douglas; David A Nicewicz
Journal:  Chem Rev       Date:  2021-09-29       Impact factor: 60.622

6.  A general deoxygenation approach for synthesis of ketones from aromatic carboxylic acids and alkenes.

Authors:  Muliang Zhang; Jin Xie; Chengjian Zhu
Journal:  Nat Commun       Date:  2018-08-29       Impact factor: 14.919

7.  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

8.  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

9.  Transition-metal-free C(sp3)-H/C(sp3)-H dehydrogenative coupling of saturated heterocycles with N-benzyl imines.

Authors:  Zhengfen Liu; Minyan Li; Guogang Deng; Wanshi Wei; Ping Feng; Quanxing Zi; Tiantian Li; Hongbin Zhang; Xiaodong Yang; Patrick J Walsh
Journal:  Chem Sci       Date:  2020-03-31       Impact factor: 9.825

10.  Bromine radical as a visible-light-mediated polarity-reversal catalyst.

Authors:  Han Wang; Haiwang Liu; Mu Wang; Meirong Huang; Xiangcheng Shi; Tonglin Wang; Xu Cong; Jianming Yan; Jie Wu
Journal:  iScience       Date:  2021-06-05
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