Literature DB >> 30417501

The Combination of Benzaldehyde and Nickel-Catalyzed Photoredox C(sp3 )-H Alkylation/Arylation.

Lumin Zhang1, Xiaojia Si1, Yangyang Yang1, Marc Zimmer1, Sina Witzel1, Kohei Sekine1, Matthias Rudolph1, A Stephen K Hashmi1,2.   

Abstract

Herein we report a highly selective photoredox C(sp3 )-H alkylation/arylation of ethers through the combination of a photo-organocatalyst (benzaldehyde) and a transition-metal catalyst (nickel). This method provides a simple and general strategy for the C(sp3 )-H alkylation/arylation of ethers. A selective late-stage modification of (-)-ambroxide has also been conducted to demonstrate the applicability of the method.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkylation; arylation; benzaldehyde; nickel catalysis; photoredox reaction

Year:  2019        PMID： 30417501     DOI： 10.1002/anie.201810526

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


  11 in total

1.  Radical C(sp3)-H functionalization and cross-coupling reactions.

Authors:  Dung L Golden; Sung-Eun Suh; Shannon S Stahl
Journal:  Nat Rev Chem       Date:  2022-05-17       Impact factor: 34.571

2.  Enantioselective Organocopper-Catalyzed Hetero Diels-Alder Reaction through in Situ Oxidation of Ethers into Enol Ethers.

Authors:  Ahmet Yesilcimen; Na-Chuan Jiang; Felix H Gottlieb; Masayuki Wasa
Journal:  J Am Chem Soc       Date:  2022-04-05       Impact factor: 16.383

3.  Mechanistic insights into photochemical nickel-catalyzed cross-couplings enabled by energy transfer.

Authors:  Rajesh Kancherla; Krishnamoorthy Muralirajan; Bholanath Maity; Safakath Karuthedath; Gadde Sathish Kumar; Frédéric Laquai; Luigi Cavallo; Magnus Rueping
Journal:  Nat Commun       Date:  2022-05-18       Impact factor: 17.694

4.  Synthetic and Mechanistic Implications of Chlorine Photoelimination in Nickel/Photoredox C(sp3)-H Cross-Coupling.

Authors:  Stavros K Kariofillis; Abigail G Doyle
Journal:  Acc Chem Res       Date:  2021-01-29       Impact factor: 22.384

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.  Diacetyl as a "traceless" visible light photosensitizer in metal-free cross-dehydrogenative coupling reactions.

Authors:  Chia-Yu Huang; Jianbin Li; Wenbo Liu; Chao-Jun Li
Journal:  Chem Sci       Date:  2019-04-08       Impact factor: 9.825

7.  Cascade Cross-Coupling of Dienes: Photoredox and Nickel Dual Catalysis.

Authors:  Long Huang; Chen Zhu; Liang Yi; Huifeng Yue; Rajesh Kancherla; Magnus Rueping
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-28       Impact factor: 15.336

8.  Visible Light-Enabled sp3 -C-H Functionalization with Chloro- and Bromoalkynes: Chemoselective Route to Vinylchlorides or Alkynes.

Authors:  Tapas Adak; Marvin Hoffmann; Sina Witzel; Matthias Rudolph; Andreas Dreuw; A Stephen K Hashmi
Journal:  Chemistry       Date:  2020-10-15       Impact factor: 5.236

9.  Regioselective Hydroalkylation and Arylalkylation of Alkynes by Photoredox/Nickel Dual Catalysis: Application and Mechanism.

Authors:  Huifeng Yue; Chen Zhu; Rajesh Kancherla; Fangying Liu; Magnus Rueping
Journal:  Angew Chem Int Ed Engl       Date:  2020-02-03       Impact factor: 15.336

Review 10.  Aldehydes as powerful initiators for photochemical transformations.

Authors:  Maria A Theodoropoulou; Nikolaos F Nikitas; Christoforos G Kokotos
Journal:  Beilstein J Org Chem       Date:  2020-04-23       Impact factor: 2.883
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