Co(dppbsa)-catalyzed reductive N,N-dimethylation of nitroaromatics with CO2 and hydrosilane

In this study, a novel half-sandwich phosphinesulfonate cobaltic complex (Co(dppbsa)) was prepared and characterized, which surprisingly enabled the chemoselective N,N-dimethylation of nitroaromatics with CO2 using NaBArF4 as the promotor and a combination of PhSiH3 and Et3SiH as the reductant. Furt...

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Published inGreen chemistry : an international journal and green chemistry resource : GC Vol. 25; no. 21; pp. 8625 - 8632
Main Authors Ma, Shuang-Shuang, Sun, Rui, Zhang, Zi-Heng, Guan, Peng-Xin, Lin, Jin-Qing, Li, Chun-Shan, Xu, Bao-Hua
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 30.10.2023
Royal Society of Chemistry
Subjects
Carbon dioxide
Catalytic activity
Chemistry
Chemistry, Multidisciplinary
Green & Sustainable Science & Technology
Green chemistry
Intermediates
Methylation
Physical Sciences
Reducing agents
Science & Technology
Science & Technology - Other Topics
FORMYLATION
CATALYSIS
NITROARENES
HYDROGENATION
LIGANDS
MECHANISM
COBALT COMPLEXES
AMINES
SELECTIVE N-METHYLATION
CARBON-DIOXIDE
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Summary:In this study, a novel half-sandwich phosphinesulfonate cobaltic complex (Co(dppbsa)) was prepared and characterized, which surprisingly enabled the chemoselective N,N-dimethylation of nitroaromatics with CO2 using NaBArF4 as the promotor and a combination of PhSiH3 and Et3SiH as the reductant. Further studies demonstrated that the catalytic activity for reduction of nitroaromatics and CO2 could be modulated, respectively, by using a specific structure and composition of hydrosilanes. The semi-reduction products nitrosoarene and silyl formate are the key intermediates affording the most efficient C-N coupling for the N,N-dimethylation of nitroaromatics with CO2.
ISSN:1463-9262
1463-9270
DOI:10.1039/d3gc02517a