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Molecules 2015, 20(4), 5409-5422; doi:10.3390/molecules20045409

Formylation of Electron-Rich Aromatic Rings Mediated by Dichloromethyl Methyl Ether and TiCl4: Scope and Limitations

1
Institute for Research in Biomedicine (IRB Barcelona), Barcelona 08028, Spain
2
Deparment of Organic Chemistry, University of Barcelona, Barcelona 08028, Spain
3
Department of Physical Chemistry, University of Barcelona, Barcelona 08028, Spain
4
Institut de Química Teòrica i Computacional (IQTCUB), University of Barcelona, Barcelona 08028, Spain
5
Institut de Biomedicina (IBUB), University of Barcelona, Barcelona 08028, Spain
6
CIBER-BBN, Barcelona 08028, Spain
7
School of Chemistry, University of KwaZulu-Natal, Durban 4000, South Africa
8
School of Chemistry, Yachay Tech, Yachay City of Knowledge, Urcuqui 100119, Ecuador
*
Authors to whom correspondence should be addressed.
Academic Editor: Jean Jacques Vanden Eynde
Received: 27 January 2015 / Revised: 8 March 2015 / Accepted: 12 March 2015 / Published: 26 March 2015
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [844 KB, uploaded 26 March 2015]   |  

Abstract

Here the aromatic formylation mediated by TiCl4 and dichloromethyl methyl ether previously described by our group has been explored for a wide range of aromatic rings, including phenols, methoxy- and methylbenzenes, as an excellent way to produce aromatic aldehydes. Here we determine that the regioselectivity of this process is highly promoted by the coordination between the atoms present in the aromatic moiety and those in the metal core. View Full-Text
Keywords: formylation; TiCl4; aromatic rings; aldehydes; dichloromethyl methyl ether formylation; TiCl4; aromatic rings; aldehydes; dichloromethyl methyl ether
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Ramos-Tomillero, I.; Paradís-Bas, M.; de Pinho Ribeiro Moreira, I.; Bofill, J.M.; Nicolás, E.; Albericio, F. Formylation of Electron-Rich Aromatic Rings Mediated by Dichloromethyl Methyl Ether and TiCl4: Scope and Limitations. Molecules 2015, 20, 5409-5422.

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