Development of efficient methods towards the synthesis of β-hydroxy carbonyls is an important area of synthetic chemistry, as these are common motifs found in numerous polyketide natural products. Accordingly, the aldol reaction has been utilized extensively towards the construction of this important motif wherein aldehydes and enolates are employed as the starting materials. Herein, a nickel-catalyzed conjunctive cross-coupling between 9-BBN borates and acyl electrophiles is reported as an alternative synthesis route to afford β-hydroxyl carbonyls. The reaction itself gives b-boryl carbonyls, but subsequent oxidation of the corresponding secondary 9-BBN borates provides the derived alcohol. One appealing feature of this transformation is that terminal alkenes, which are easily accessible, can be employed as the starting material and derived to the corresponding β-hydroxyl carbonyls in a one-pot fashion. This reaction is highly practical as it can be run at ambient temperature, requires reaction time as short as 2 minutes, and employs cheap commercially available nickel catalyst.

Applications of conjunctive cross-coupling towards the synthesis of β-hydroxy ketones

2019 Spring National Meeting

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