Borylative Desymmetrization of multifunctional haloarenes assisted by sodium dispersion

05 September 2024, Version 2
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Multiply halogenated aromatic compounds were selectively borylated by a boron alkoxide in the presence of sodium dispersion when the reaction was carried out at a low temperature, while multi-functionalization took place at an elevated temperature. The reaction of 1,4-dichlorobenzene with sodium dispersion (200–1200 mol%) in the presence of isopropyloxyboron pinacolate (120–240 mol%) afforded (4-chlorophenyl)boron pinacolate in up to 84% yield. Formation of diborylated product hardly accompanied under the reaction conditions at –78 °C for 1 h.

Keywords

borylation
sodium dispersion
dihaloarene

Supplementary materials

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Description
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Supporting Information
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Experimental details and details on DFT calculation
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