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Cu2O Nanocrystals-Catalyzed Photoredox Sonogashira Coupling of Terminal Alkynes and Arylhalides Enhanced by CO2
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Cu2O Nanocrystals-Catalyzed Photoredox Sonogashira Coupling of Terminal Alkynes and Arylhalides Enhanced by CO2

Munusamy Shanmugam, Arunachalam Sagadevan, Vaibhav Pramod Charpe, V. Kishore Kumar Pampana 和 Kuo Chu Hwang
ChemSusChem, 卷.13(2), 頁碼.287-292
19/01/2020
PMID: 31476259
Web of Science ID: WOS:000488192400001

摘要

Chemistry Chemistry, Multidisciplinary Green & Sustainable Science & Technology Physical Sciences Science & Technology Science & Technology - Other Topics
Herein the first visible-light-activated Sonogashira C-C coupling reaction at room temperature catalyzed by single-metal heterogeneous Cu2O truncated nanocubes (Cu2O TNCs) was developed. A wide variety of aryl halides and terminal alkynes worked well in this recyclable heterogeneous photochemical process to form the corresponding Sonogashira C-C coupling products in good yields. Mechanistic control studies indicated that CO2 enhances the formation of light-absorbing heterogeneous surface-bound Cu-I-phenylacetylide (lambda(max)=472 nm), which further undergoes single-electron transfer with aryl iodides/bromides to enable Sonogashira Csp2-C-sp bond formation. In contrast to literature-reported bimetallic TiO2-containing nanoparticles as photocatalyst, this work avoided the need of cocatalysis by TiO2. Single-metal Cu-I in Cu2O TNCs was solely responsible for the observed Csp2-C-sp coupling reactions under CO2 atmosphere.

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