High throughput synthesis of 2,5-substituted indoles using a titanium carbenoid bearing boronate functionality

Main, C.A., Petersson, H.M., Rahman, S.S. and Hartley, R.C. (2008) High throughput synthesis of 2,5-substituted indoles using a titanium carbenoid bearing boronate functionality. Tetrahedron, 64(5), pp. 901-914. (doi:10.1016/j.tet.2007.08.119)

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Abstract

A titanium benzylidene complex bearing a boronate group converted resin-bound esters into enol ethers. Suzuki cross-coupling with aryl iodides followed by cleavage with acid completed the solid-phase synthesis of 2,5-disubstituted N-Boc-indoles. Also reported is the use of tert-butyllithium and 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane to convert an aryl bromide into an arylboronate in the presence of a dithiane, with simultaneous reduction of an aryl azide to an amine.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Hartley, Professor Richard
Authors: Main, C.A., Petersson, H.M., Rahman, S.S., and Hartley, R.C.
Subjects:Q Science > QD Chemistry
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Tetrahedron
Publisher:Elsevier
ISSN:0040-4020
Published Online:24 October 2007
Copyright Holders:Copyright © 2007 Elsevier
First Published:First published in Tetrahedron 64(5):901-914
Publisher Policy:Reproduced in accordance with the copyright policy of the publisher

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