Issue 15, 2019

BODIPY as electron withdrawing group for the activation of double bonds in asymmetric cycloaddition reactions

Abstract

In this work we have found that a BODIPY can be used as an electron withdrawing group for the activation of double bonds in asymmetric catalysis. The synthesis of cyclohexyl derivatives containing a BODIPY unit can easily be achieved via trienamine catalysis. This allows a new different asymmetric synthesis of BODIPY derivatives and opens the door to future transformation of this useful fluorophore. In addition, the Quantum Chemistry calculations and mechanistic studies provide insights into the role of BODIPY as an EWG.

Graphical abstract: BODIPY as electron withdrawing group for the activation of double bonds in asymmetric cycloaddition reactions

Supplementary files

Article information

Article type
Edge Article
Submitted
25 Febr. 2019
Accepted
13 Marts 2019
First published
20 Marts 2019
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., 2019,10, 4346-4351

BODIPY as electron withdrawing group for the activation of double bonds in asymmetric cycloaddition reactions

A. Guerrero-Corella, J. Asenjo-Pascual, T. J. Pawar, S. Díaz-Tendero, A. Martín-Sómer, C. V. Gómez, J. L. Belmonte-Vázquez, D. E. Ramírez-Ornelas, E. Peña-Cabrera, A. Fraile, D. C. Cruz and J. Alemán, Chem. Sci., 2019, 10, 4346 DOI: 10.1039/C9SC00959K

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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