Electrochemical Hydroboration of Alkynes

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Chemo-, regio-, and stereoselective iron-catalysed hydroboration of alkenes and alkynes.

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.

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Metal-free homoallylic oxygen-directed intramolecular hydroboration is reported. Regioselectivities from 20:1 to 82:1 favoring the 1,3-dioxy-substituted products have been achieved using Me2S.BH3/TfOH followed by standard oxidative workup. Branching at the C5 position improves regioselectivity.

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A b-diketiminato n-butylmagnesium complex is presented as a selective precatalyst for the reductive hydroboration of organic nitriles with pinacolborane (HBpin). Stoichiometric reactivity studies indicate that catalytic turnover ensues through the generation of magnesium aldimido, aldimidoborate and borylamido intermediates, which are formed in a sequence of intramolecular nitrile insertion and...

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Magnesium-catalysed hydroboration of isonitriles.

A β-diketiminato magnesium alkyl complex is shown to be an effective pre-catalyst for the first reported catalytic hydroboration of organic isonitriles, RNC, with HBpin. The reaction proceeds under mild conditions when R = alkyl and provides access to the corresponding 1,2-diborylated amine products.

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A chemo-, regio-, and stereoselective iron-catalyzed 1,4-hydroboration of dienes that affords gamma-disubstituted allylboranes has been developed. 1,4-Hydroboration of 2-substituted dienes forms allylborane products with (E)-trisubstituted double bonds exclusively.

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ژورنال

عنوان ژورنال: Chemistry – A European Journal

سال: 2021

ISSN: 0947-6539,1521-3765

DOI: 10.1002/chem.202101132