NDLI: Activation of CH Bonds through Oxidant-Free Photoredox Catalysis: Cross-Coupling Hydrogen-Evolution Transformation of Isochromans and β-Keto Esters

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Activation of CH Bonds through Oxidant-Free Photoredox Catalysis: Cross-Coupling Hydrogen-Evolution Transformation of Isochromans and β-Keto Esters

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Zheng, Yi-wen Li, Zhi-jun Li, Jia-xin Xiang, Ming Meng, Qing-yuan Ye, Chen Chen, Bin Tung, Chen-ho Wu, Li-zhu
Description	Author Affiliation: Xiang M ( Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry & University of Chinese Academy of Sciences, Chinese Academy of Sciences, Beijing 100190 (P. R. China).); Meng QY ( Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry & University of Chinese Academy of Sciences, Chinese Academy of Sciences, Beijing 100190 (P. R. China).); Li JX ( Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry & University of Chinese Academy of Sciences, Chinese Academy of Sciences, Beijing 100190 (P. R. China).); Zheng YW ( School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100 (P. R. China).); Ye C ( Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry & University of Chinese Academy of Sciences, Chinese Academy of Sciences, Beijing 100190 (P. R. China).); Li ZJ ( Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry & University of Chinese Academy of Sciences, Chinese Academy of Sciences, Beijing 100190 (P. R. China).); Chen B ( Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry & University of Chinese Academy of Sciences, Chinese Academy of Sciences, Beijing 100190 (P. R. China).); Tung CH ( Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry & University of Chinese Academy of Sciences, Chinese Academy of Sciences, Beijing 100190 (P. R. China).); Wu LZ ( Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry & University of Chinese Academy of Sciences, Chinese Academy of Sciences, Beijing 100190 (P. R. China). lzwu@mail.ipc.ac.cn.)
Abstract	The direct and controlled activation of a $C(sp^{3})H$ bond adjacent to an O atom is of particular synthetic value for the conventional derivatization of ethers or alcohols. In general, stoichiometric amounts of an oxidant are required to remove an electron and a hydrogen atom of the ether for subsequent transformations. Herein, we demonstrate that the activation of a CH bond next to an O atom could be achieved under oxidant-free conditions through photoredox-neutral catalysis. By using a commercial dyad photosensitizer $(Acr^{+}-Mes$ $ClO_{4}^{−},$ 9-mesityl-10-methylacridinium perchlorate) and an easily available cobaloxime complex $(Co(dmgBF_{2})_{2}⋅2 MeCN,$ dmg=dimethylglyoxime), the nucleophilic addition of β-keto esters to oxonium species, which is rarely observed in photocatalysis, leads to the corresponding coupling products and $H_{2}$ in moderate to good yields under visible-light irradiation. Mechanistic studies suggest that both isochroman and the cobaloxime complex quench the electron-transfer state of this dyad photosensitizer and that benzylic CH bond cleavage is probably the rate-determining step of this cross-coupling hydrogen-evolution transformation.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	50
Volume Number	21
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2015-12-07
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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