Reductive CO2 Fixation via the Selective Formation of C–C Bonds: Bridging Enaminones and Synthesis of 1,4-Dihydropyridines

Herein, a selective tandem C–C bond-forming reaction with CO2 was developed to realize the bridging of enaminones and synthesis of 1,4-dihydropyridines, respectively. n-Butylamine significantly promoted this CO2 deoxymethylenation procedure catalyzed by 1,5,7-triazabicyclo[4.4.0]­dec-5-ene (TBD) and...

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Veröffentlicht in:Organic letters 2020-11, Vol.22 (21), p.8326-8331
Hauptverfasser: Zhao, Yulei, Guo, Xuqiang, Ding, Xin, Zhou, Zheng, Li, Man, Feng, Nan, Gao, Bowen, Lu, Xu, Liu, Yunlin, You, Jinmao
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Sprache:eng
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Zusammenfassung:Herein, a selective tandem C–C bond-forming reaction with CO2 was developed to realize the bridging of enaminones and synthesis of 1,4-dihydropyridines, respectively. n-Butylamine significantly promoted this CO2 deoxymethylenation procedure catalyzed by 1,5,7-triazabicyclo[4.4.0]­dec-5-ene (TBD) and ZnCl2. The mechanism involving the formation of bis­(silyl)­acetal, nucleophilic addition, and amine elimination was also interpreted to clarify the bridging of two molecules of enaminones with CO2 and the generation of dihydropyridine derivatives.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c02963