The direct trifluoromethylsilylation and cyanosilylation of aldehydes via an electrochemically induced intramolecular pathway

The initiator-free electrochemical trifluoromethylsilylation and cyanosilylation of aldehydes were developed in an undivided cell. A DFT study reveals that the direct cathodic activation of trimethylsilyl reagents significantly released the congestion around the 'Si' atom, allowing the Si-...

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Published inChemical communications (Cambridge, England) Vol. 56; no. 16; pp. 2435 - 2438
Main Authors Yang, Hui, Shen, Yongli, Xiao, Zihui, Liu, Caiyan, Yuan, Kedong, Ding, Yi
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 25.02.2020
Royal Society of Chemistry
Subjects
Aldehydes
Chemistry
Chemistry, Multidisciplinary
Initiators
Physical Sciences
Reagents
Science & Technology
NUCLEOPHILIC TRIFLUOROMETHYLATION
MILD
REAGENTS
LEWIS-BASE ACTIVATION
CARBONYL-COMPOUNDS
CYANATION
FLUORINE
N-HETEROCYCLIC CARBENES
TRIMETHYLSILYL CYANIDE
EFFICIENT
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Summary:The initiator-free electrochemical trifluoromethylsilylation and cyanosilylation of aldehydes were developed in an undivided cell. A DFT study reveals that the direct cathodic activation of trimethylsilyl reagents significantly released the congestion around the 'Si' atom, allowing the Si-O bond affinity to form concerted anion intermediates with aldehydes. Thus, intramolecular -CF3 and -CN migration make the reactions much easier to carry out without initiators.
Bibliography:ObjectType-Article-1
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ISSN:1359-7345
1364-548X
DOI:10.1039/c9cc08975f