Triarylboranes Bearing ( <i>ortho</i> -Carboran-1-yl)aryl Groups for Catalytic Hydrogenation with Pure or Crude H <sub>2</sub>

Structural diversification of triarylboranes with unexplored substituents can expand their applications in organic synthesis. We synthesized triarylboranes that bear 2,6-F<sub>2</sub>-4-(<i>o</i>-carboran-1-yl)phenyl (Ar) groups and evaluated their Lewis acidity and catalytic activity. B(2,6-Cl<sub>2</sub>C<sub>6</sub>H<sub>3</sub>)Ar<sub>2</sub> exhibited high activity in the hydrogenation of <i>N</i>-heteroaromatics using pure (TON = up to 3960) and crude H<sub>2</sub> (TON = up to 2400). This borane also catalyzes the dehydrogenation of tetrahydroquinoline and the reductive alkylation of aliphatic amino-acid esters with H<sub>2</sub>, demonstrating the first catalytic applications of carboranyl-substituted triarylboranes in diverse molecular transformations.

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Publication Details

Journal
Organic Letters
Published
2025-12-26
DOI
https://doi.org/10.1021/acs.orglett.5c04669
Citations
1
Primary Topic
Boron Compounds in Chemistry
Type
article
Field-Weighted Citation Impact
1.36
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article

Triarylboranes Bearing ( ortho -Carboran-1-yl)aryl Groups for Catalytic Hydrogenation with Pure or Crude H 2

Anil Chauhan, Yusei Hisata, Yoichi Hoshimoto, Riku Ikeda
1 citations
Organic Letters
Boron Compounds in Chemistry
1.36
article

Triarylboranes Bearing ( ortho -Carboran-1-yl)aryl Groups for Catalytic Hydrogenation with Pure or Crude H 2

Anil Chauhan, Yusei Hisata, Yoichi Hoshimoto, Riku Ikeda
article en
1 citations

Abstract

Structural diversification of triarylboranes with unexplored substituents can expand their applications in organic synthesis. We synthesized triarylboranes that bear 2,6-F<sub>2</sub>-4-(<i>o</i>-carboran-1-yl)phenyl (Ar) groups and evaluated their Lewis acidity and catalytic activity. B(2,6-Cl<sub>2</sub>C<sub>6</sub>H<sub>3</sub>)Ar<sub>2</sub> exhibited high activity in the hydrogenation of <i>N</i>-heteroaromatics using pure (TON = up to 3960) and crude H<sub>2</sub> (TON = up to 2400). This borane also catalyzes the dehydrogenation of tetrahydroquinoline and the reductive alkylation of aliphatic amino-acid esters with H<sub>2</sub>, demonstrating the first catalytic applications of carboranyl-substituted triarylboranes in diverse molecular transformations.

Organic LettersVol. 28(1)
Institute for Schools of the Future (US), Graduate School USA (US)
Openalex Percentile: Top 13%
Boron Compounds in Chemistry
1.36
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