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The development and mechanistic investigation of a palladium-catalyzed 1,3-arylfluorination of chromenes

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Abstract

A mild palladium-catalyzed ligand-controlled regioselective 1,3-arylfluorination of 2[H]-chromenes has been developed. The products with a syn-1,3 substitution pattern were obtained with high enantiomeric excess using a PyrOx ligand, wherein the utility of these pyranyl-fluorides was further demonstrated through their participation in a diastereoselective C–C bond forming reaction. Ligand dependent divergent formation of both the 1,3- and 1,2- alkene difunctionalization products was observed. The nature of this bifurcation was investigated through experimental studies in combination with computational and statistical analysis tools. Ultimately, the site selectivity was found to rely on ligand denticity and metal electrophilicity, the electronics of the boronic acid, and the donor ability of the directing group in the substrate.

Graphical abstract: The development and mechanistic investigation of a palladium-catalyzed 1,3-arylfluorination of chromenes

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Article information


Submitted
19 Nov 2016
Accepted
23 Jan 2017
First published
09 Feb 2017

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2017,8, 2890-2897
Article type
Edge Article

The development and mechanistic investigation of a palladium-catalyzed 1,3-arylfluorination of chromenes

R. T. Thornbury, V. Saini, T. D. A. Fernandes, C. B. Santiago, E. P. A. Talbot, M. S. Sigman, J. M. McKenna and F. D. Toste, Chem. Sci., 2017, 8, 2890
DOI: 10.1039/C6SC05102B

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