Evaluation of 3,3′-Triazolyl Biisoquinoline N,N′-Dioxide Catalysts for Asymmetric Hydrosilylation of Hydrazones with Trichlorosilane

Authors

Shiyu Sun, Florida Institute of Technology - Melbourne
Changgong Xu, Florida Institute of Technology - Melbourne
Jamielyn Jarvis, Florida Institute of Technology - Melbourne
Phillip Nader, Florida Institute of Technology - Melbourne
Brandon Naumann, Florida Institute of Technology - Melbourne
Abigail Soliven, Purdue University
Roberto Peverati, Florida Institute of Technology - Melbourne
Noriko Takenaka, Florida Institute of Technology - Melbourne

Abstract

A new class of axial-chiral biisoquinoline N,N′-dioxides was evaluated as catalysts for the enantioselective hydrosilylation of acyl hydrazones with trichlorosilane. While these catalysts provided poor to moderate reactivity and enantioselectivity, this study represents the first example of the organocatalytic asymmetric reduction of acyl hydrazones. In addition, the structures and energies of two possible diastereomeric catalyst–trichlorosilane complexes (2a–HSiCl₃) were analyzed using density functional theory calculations.

Comments

This article is published under a CC-BY license.

Sun, S.; Xu, C.; Jarvis, J.; Nader, P.; Naumann, B.; Soliven, A.; Peverati, R.; Takenaka, N. Evaluation of 3,3′-Triazolyl Biisoquinoline N,N′-Dioxide Catalysts for Asymmetric Hydrosilylation of Hydrazones with Trichlorosilane. Catalysts 2021, 11, 1103. https://doi.org/10.3390/catal11091103

Keywords

Lewis base catalysis; trichlorosilane; hydrosilylation; hydrazone; computational chemistry

Date of this Version

9-14-2021

DOI

/10.3390/catal11091103

Recommended Citation

Sun, S.; Xu, C.; Jarvis, J.; Nader, P.; Naumann, B.; Soliven, A.; Peverati, R.; Takenaka, N. Evaluation of 3,3′-Triazolyl Biisoquinoline N,N′-Dioxide Catalysts for Asymmetric Hydrosilylation of Hydrazones with Trichlorosilane. Catalysts 2021, 11, 1103. https://doi.org/10.3390/catal11091103