Abstract
The highly chemo-, regio-, and stereoselective synthesis of alkyl- and vinyl boronic esters with good functional group tolerance has been developed using in situ activation of a bench-stable iron(II) pre-catalyst and pinacolborane (16 examples, 45-95% yield, TOF up to 30,000 mol h(-1)). The first iron-catalysed alkene hydrogermylation is also reported.
Highlights
The highly chemo, regio, and stereoselective synthesis of alkyland vinyl boronic esters with good functional group tolerance has been developed using in situ activation of a bench-stable iron(II) pre-catalyst and pinacolborane (16 examples, 45–95% yield, TOF up to 30 000 mol hÀ1)
Alkyl boronic esters are commonly prepared by reaction of alkyllithium and magnesium reagents with a boron source;1a these methods are limited by poor functional-group tolerance and atom economy
The copper-catalysed synthesis of alkyl boronic esters from primary and secondary alkyl halides has been reported with good functional group tolerance,2e long reaction times, excess B2pin[2], and relatively high catalyst loadings were required
Summary
The highly chemo-, regio-, and stereoselective synthesis of alkyland vinyl boronic esters with good functional group tolerance has been developed using in situ activation of a bench-stable iron(II) pre-catalyst and pinacolborane (16 examples, 45–95% yield, TOF up to 30 000 mol hÀ1). We report the iron-catalysed hydroboration of alkenes and alkynes using a bench stable iron(II) pre-catalyst and pinacolborane to give alkyl and vinyl boronic esters directly.
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