Palladium-catalyzed <i>B</i>-Diarylation of Diethylaminoborane for the Synthesis of Diarylborinic Acids

Shimazumi, Ryoma; Igarashi, Takuya; Tobisu, Mamoru

doi:10.1246/cl.200213

Cited by 2 publications

(3 citation statements)

References 34 publications

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“…Later on, the approach was extended to the synthesis of acyclic borinic acid derivatives by the same group [ 54 ]. As mentioned above, the use of DIPOB only resulted in the formation of boronic acids under palladium catalysis.…”

Section: Formation Of Two Carbon–boron Bondsmentioning

confidence: 99%

Recent Advances in the Synthesis of Borinic Acid Derivatives

2023

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Borinic acids [R2B(OH)] and their chelate derivatives are a subclass of organoborane compounds used in cross-coupling reactions, catalysis, medicinal chemistry, polymer or optoelectronics materials. In this paper, we review the recent advances in the synthesis of diarylborinic acids and their four-coordinated analogs. The main strategies to build up borinic acids rely either on the addition of organometallic reagents to boranes (B(OR)3, BX3, aminoborane, arylboronic esters) or the reaction of triarylboranes with a ligand (diol, amino alcohol, etc.). After general practical considerations of borinic acids, an overview of the main synthetic methods, their scope and limitations is provided. We also discuss some mechanistic aspects.

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Section: Formation Of Two Carbon–boron Bondsmentioning

confidence: 99%

Recent Advances in the Synthesis of Borinic Acid Derivatives

2023

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“…[17] Switching to less bulky aminoboranes such as diethylaminoborane allowed extending this double B-arylation reaction to an intermolecular version. [18] Despite these new synthetic approaches, the synthesis of unsymmetrical arylborinic acids has not been widely reported. [15a,15c,16a,17,18] Our group has recently been developing borinic acid-based sensors as a new powerful tool for hydrogen peroxide detection.…”

Section: Introductionmentioning

confidence: 99%

“…reported an intramolecular palladium‐catalyzed borylation of dihalides using diisopropylaminoborane as a boron source providing cyclic borinic acids [17] . Switching to less bulky aminoboranes such as diethylaminoborane allowed extending this double B‐arylation reaction to an intermolecular version [18] . Despite these new synthetic approaches, the synthesis of unsymmetrical arylborinic acids has not been widely reported [15a,c,16a,17,18] …”

Section: Introductionmentioning

confidence: 99%