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Synfacts 2022; 18(08): 0867
DOI: 10.1055/s-0041-1738238
Metals in Synthesis

Take Et instead of Me: Preparation and Application of a Novel Class of Stable Arylboronic Esters

Contributor(s):
Martin Oestreich
,
Hendrik F. T. Klare
,
Lucie Finck
Oka N, Yamada T, Sajiki H, Akai S, *, Ikawa T. * Osaka University and Gifu Pharmaceutical University, Japan
Aryl Boronic Esters Are Stable on Silica Gel and Reactive under Suzuki–Miyaura Coupling Conditions.

Org. Lett. 2022;
24: 3510-3514
DOI: 10.1021/acs.orglett.2c01174.
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Key words

aryl boronic esters - Suzuki–Miyaura cross-coupling - 1,1,2,2-tetraethylene glycol (Epin)

Significance

The synthesis and application of arylboronic 1,1,2,2-tetraethylethylene glycol esters, Ar–B(Epin), is disclosed. These aryl boronates are readily accessible via dehydrative esterification of boronic acids, metalation of aryl bromides or Miyaura borylation. Substitution of the methyl units of the pinacol esters Ar–Bpin by ethyl groups leads to higher stability, and the corresponding arylboronic esters Ar–B(Epin) are easily purified by column chromatography on silica gel.


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Comment

The novel arylboronic esters show enhanced reactivity in Suzuki–Miyaura cross-couplings, providing the coupling products in excellent yields. These organoboron compounds represent a viable alternative to the commonly used aryl boronic acids or pinacol esters.


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Publication History

Article published online:
18 July 2022

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