[BO<sub>2</sub>]<sup>−</sup> as a Synthon for the Generation of Boron‐Centered Carbamate and Carboxylate Isosteres

An efficient synthesis of an acid‐free neutral oxoborane of the type carboranyl‐B(carbene)=O has been developed via a serendipitous discovery from the reaction of 1,2‐[BBr(carbene)]‐o‐carborane with AgOTf. This represents a new type of oxoborane. The stabilization of this oxoborane may be attributed to 1) kinetic stabilization provided by a bulky 3D carboranyl ligand and 2) thermodynamic stabilization offered by a carbene ligand. Crystallographic analyses support the presence of the shortest terminal B=O double bond ever reported thus far. Its reactivity has also been examined.

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Acid–Base Free Main Group Carbonyl Analogues

Loh

Aldridge

2020

Angew Chem Int Ed

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[BO₂]⁻ as a Synthon for the Generation of Boron‐Centered Carbamate and Carboxylate Isosteres

Abstract: Oxoborane carbamate and carboxylate analogues result from the in situ trapping of [BO2]− produced by elimination of 2,3‐dimethyl‐2‐butene from a pinacolatoboryl anion.

Cited by 7 publications

References 65 publications

Acid–Base Free Main Group Carbonyl Analogues

Acid–Base Free Main Group Carbonyl Analogues

Synthesis, Structure, and Reactivity of Acid‐Free Neutral Oxoborane

Acid–Base Free Main Group Carbonyl Analogues

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[BO2]− as a Synthon for the Generation of Boron‐Centered Carbamate and Carboxylate Isosteres

Abstract: Oxoborane carbamate and carboxylate analogues result from the in situ trapping of [BO2]− produced by elimination of 2,3‐dimethyl‐2‐butene from a pinacolatoboryl anion.

Cited by 7 publications

References 65 publications

Acid–Base Free Main Group Carbonyl Analogues

Acid–Base Free Main Group Carbonyl Analogues

Synthesis, Structure, and Reactivity of Acid‐Free Neutral Oxoborane

Acid–Base Free Main Group Carbonyl Analogues

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Product

Resources

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[BO₂]⁻ as a Synthon for the Generation of Boron‐Centered Carbamate and Carboxylate Isosteres