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 |
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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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