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Titanium promoted reduction of imines with Grignards, silanes, and zinc: identification of a new mechanism with silanes

Kumar, Akshai and Pandiakumar, Arun Kumar and Samuelson, AG (2014) Titanium promoted reduction of imines with Grignards, silanes, and zinc: identification of a new mechanism with silanes. In: TETRAHEDRON, 70 (19). pp. 3185-3190.

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Official URL: http://dx.doi.org/10.1016/j.tet.2014.03.035

Abstract

Aldimines react with reducing agents, such as Grignards, phenylsilane or zinc in the presence of titanium(IV) isopropoxide to form amines and reductively coupled imines (diamines). Using deuterium labeled reagents, the mechanism of reduction to form amines is described. Reducing agents, such as the Grignard and zinc result in the formation of low valent titanium (LVT), which in turn reduces the imine. On the other hand, phenylsilane reacts by a distinctly different mechanism and where a hydrogen atom from silicon is directly transferred to the titanium coordinated imine. (c) 2014 Elsevier Ltd. All rights reserved.

Item Type: Journal Article
Additional Information: Copyright for this article belongs to the PERGAMON-ELSEVIER SCIENCE LTD, ENGLAND
Keywords: Deuterium labeling; Low valent titanium; Grignard; Phenylsilane; Zinc
Department/Centre: Division of Chemical Sciences > Inorganic & Physical Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 11 Jun 2014 09:36
Last Modified: 11 Jun 2014 09:36
URI: http://eprints.iisc.ac.in/id/eprint/49161

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