Issue 5, 2018

The vinylogous Catellani reaction: a combined computational and experimental study

Abstract

In the presence of 5 mol% Pd(OAc)2, 1 equiv. of norbornene, and K2CO3, the reaction of 4-iodo-2-quinolones with tertiary o-bromobenzylic alcohols produced the desired benzopyran-fused 2-quinolones in moderate to high yields. A Catellani-type mechanism involving vinylic C–H cleavage is proposed based on the results of control experiments and density functional theory calculations.

Graphical abstract: The vinylogous Catellani reaction: a combined computational and experimental study

Supplementary files

Article information

Article type
Edge Article
Submitted
30 Sep 2017
Accepted
29 Nov 2017
First published
30 Nov 2017
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2018,9, 1191-1199

The vinylogous Catellani reaction: a combined computational and experimental study

Y. Yamamoto, T. Murayama, J. Jiang, T. Yasui and M. Shibuya, Chem. Sci., 2018, 9, 1191 DOI: 10.1039/C7SC04265E

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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