ãChemodivergent transformations of amides using gem-diborylalkanes as pro-nucleophilesã?was published in Nature Communications in 2020. These research results belong to Sun, Wei; Wang, Lu; Hu, Yue; Wu, Xudong; Xia, Chungu; Liu, Chao. Formula: C13H26B2O4 The article mentions the following:
A chemodivergent transformation of primary, secondary and tertiary amides by using 1,1-diborylalkanes as pro-nucleophiles was disclosed. In general, selective B-O elimination occurred for primary, secondary amides and tertiary lactams to generated enamine intermediate, while tertiary amides undergo B-N elimination to generated enolate intermediate. Various in-situ electrophilic trapping of those intermediates allowed the chemoselective synthesis of α-functionalized ketones, β-aminoketones, enamides, β-ketoamides, γ-aminoketones and cyclic amines from primary, secondary, tertiary amides and lactams. The key for these transformations was the enolization effect after the addition of α-boryl carbanion to amides. The experimental process involved the reaction of Bis[(pinacolato)boryl]methane(cas: 78782-17-9Formula: C13H26B2O4)
Bis[(pinacolato)boryl]methane(cas: 78782-17-9) belongs to organoboron compounds.Formula: C13H26B2O4 Organoboron compounds have been a cornerstone of synthetic transformations for decades. Areas such as boron-containing catalysts, metalate chemistry, photoredox methods, and boryl anions have brought significant new developments in understanding and provided new reactivity upon.
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