Issue 31, 2021

Hydrosilylation and Mukaiyama aldol-type reaction of quinolines and hydrosilylation of imines catalyzed by a mesoionic carbene-stabilized borenium ion

Abstract

Aldimines and ketimines containing electron-donating and electron-withdrawing groups can be hydrosilylated with borenium catalysts at as low as 1 mol% catalyst loading at room temperature, providing the corresponding secondary amines in excellent yields. Reactions with 2-phenylquinoline gave the 1,4-hydrosilylquinoline product selectively which can be further functionalized in a one-pot synthesis to give unique γ-amino alcohol derivatives. Control experiments suggest that the borenium ion catalyzes both the hydrosilylation and subsequent addition to the aldehyde.

Graphical abstract: Hydrosilylation and Mukaiyama aldol-type reaction of quinolines and hydrosilylation of imines catalyzed by a mesoionic carbene-stabilized borenium ion

Supplementary files

Article information

Article type
Communication
Submitted
31 מאי 2021
Accepted
02 יול 2021
First published
02 יול 2021

Org. Biomol. Chem., 2021,19, 6786-6791

Hydrosilylation and Mukaiyama aldol-type reaction of quinolines and hydrosilylation of imines catalyzed by a mesoionic carbene-stabilized borenium ion

J. J. Clarke, K. Devaraj, B. P. Bestvater, R. Kojima, P. Eisenberger, J. F. DeJesus and C. M. Crudden, Org. Biomol. Chem., 2021, 19, 6786 DOI: 10.1039/D1OB01056E

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