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Issue 9, 2019
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An atom efficient synthesis of tamoxifen

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Abstract

The direct carbolithiation of diphenylacetylenes and their cross-coupling procedure taking advantage of the intermediate alkenyllithium reagents are presented. By employing our recently discovered highly active palladium nanoparticle based catalyst, we were able to couple an alkenyllithium reagent with a high (Z/E) selectivity (10 : 1) and good yield to give the breast cancer drug tamoxifen in just 2 steps from commercially available starting materials and with excellent atom economy and reaction mass efficiency.

Graphical abstract: An atom efficient synthesis of tamoxifen

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Supplementary files

Article information


Submitted
29 Nov 2018
Accepted
28 Jan 2019
First published
28 Jan 2019

This article is Open Access

Org. Biomol. Chem., 2019,17, 2315-2320
Article type
Communication

An atom efficient synthesis of tamoxifen

D. Heijnen, M. van Zuijlen, F. Tosi and B. L. Feringa, Org. Biomol. Chem., 2019, 17, 2315
DOI: 10.1039/C8OB02977F

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