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Published on: May 26, 2019
Tetrahydroxydiboron-Promoted Radical Addition of Alkynols
Ze-Ying Sun1, Sen Zhou1, Kai Yang1
1Tianjin Key Laboratory of Molecular Optoelectronic Science, Department of Chemistry, School of Science, Tianjin University, Tianjin 300072, P. R. China.
Abstract:
Tetrahydroxydiboron has previously been used as a borylation or reducing reagent in organic synthesis. Herein, we present a novel tetrahydroxydiboron-promoted radical addition of internal alkynes followed by intramolecular oxidation of alcohol through 1,5-hydrogen atom transfer. Preliminary mechanistic studies showed that the process might be initiated through N,N-dimethylformamide-assisted homolytic cleavage of tetrahydroxydiboron. This process provides a convenient synthesis of fluoroalkyl-substituted alkenes with a pendant aldehyde or ketone moiety.
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