Issue 21, 2021

The synthesis, properties, and reactivity of Lewis acidic aminoboranes

Abstract

The evolution of frustrated Lewis pair chemistry has led to significant research into the development of new Lewis acidic boranes. Much of this has focused on modifying aryl substituents rather than introducing heteroatoms bound to boron. We recently reported that bis(pentafluorophenyl)phenothiazylborane (1) could be used as a Lewis acid catalyst for the heterolytic dehydrocoupling of stannanes. In this work, we synthesize and characterize a family of Lewis acidic aminoboranes and explored their reactivity with various Lewis bases as well as their efficacy as catalysts for stannane dehydrocoupling and hydrosilylation. Quantum chemical calculations were undertaken to understand the origins of the Lewis acidity and the most Lewis acidic aminoborane (5) was found to be an effective catalyst even in coordinating solvents such as water or acetonitrile, suggesting the amino substituent provides a level of protection against competing donors.

Graphical abstract: The synthesis, properties, and reactivity of Lewis acidic aminoboranes

Supplementary files

Article information

Article type
Paper
Submitted
17 Mar 2021
Accepted
04 May 2021
First published
04 May 2021

Org. Biomol. Chem., 2021,19, 4796-4802

The synthesis, properties, and reactivity of Lewis acidic aminoboranes

J. N. Bentley, S. A. Simoes, E. Pradhan, T. Zeng and C. B. Caputo, Org. Biomol. Chem., 2021, 19, 4796 DOI: 10.1039/D1OB00520K

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