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Triarylboranes Bearing (ortho-Carboran-1-yl)aryl Groups for Catalytic Hydrogenation with Pure or Crude H2
Yusei Hisata1, Riku Ikeda1, Anil Chauhan1
1Department of Applied Chemistry, Graduate School of Engineering, The University of Osaka, Suita, Osaka 565-0871, Japan.
Abstract:
Structural diversification of triarylboranes with unexplored substituents can expand their applications in organic synthesis. We synthesized triarylboranes that bear 2,6-F2-4-(o-carboran-1-yl)phenyl (Ar) groups and evaluated their Lewis acidity and catalytic activity. B(2,6-Cl2C6H3)Ar2 exhibited high activity in the hydrogenation of N-heteroaromatics using pure (TON = up to 3960) and crude H2 (TON = up to 2400). This borane also catalyzes the dehydrogenation of tetrahydroquinoline and the reductive alkylation of aliphatic amino-acid esters with H2, demonstrating the first catalytic applications of carboranyl-substituted triarylboranes in diverse molecular transformations.
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