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

By C.A. Main, H.M. Petersson, S.S. Rahman and R.C. Hartley

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

Topics: QD
Publisher: Elsevier
Year: 2008
OAI identifier: oai:eprints.gla.ac.uk:44842
Provided by: Enlighten

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Citations

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