Formylation of electron-rich aromatic rings mediated by dichloromethyl methyl ether and TiCl4: scope and limitations

Iván Ramos-Tomillero; Marta Paradís-Bas; Ibério de Pinho Ribeiro Moreira; Josep María Bofill; Ernesto Nicolás; Fernando Albericio

doi:10.3390/molecules20045409

Formylation of electron-rich aromatic rings mediated by dichloromethyl methyl ether and TiCl4: scope and limitations

Molecules. 2015 Mar 26;20(4):5409-22. doi: 10.3390/molecules20045409.

Authors

Iván Ramos-Tomillero^{1

2}, Marta Paradís-Bas^{1

2}, Ibério de Pinho Ribeiro Moreira^{3

4}, Josep María Bofill^{2

5}, Ernesto Nicolás^{6

7}, Fernando Albericio^{8

9

10

11

12}

Affiliations

¹ Institute for Research in Biomedicine (IRB Barcelona), Barcelona 08028, Spain. jmbofill@ub.edu.
² Deparment of Organic Chemistry, University of Barcelona, Barcelona 08028, Spain. jmbofill@ub.edu.
³ Department of Physical Chemistry, University of Barcelona, Barcelona 08028, Spain. i.moreira@ub.edu.
⁴ Institut de Química Teòrica i Computacional (IQTCUB), University of Barcelona, Barcelona 08028, Spain. i.moreira@ub.edu.
⁵ Institut de Química Teòrica i Computacional (IQTCUB), University of Barcelona, Barcelona 08028, Spain. jmbofill@ub.edu.
⁶ Deparment of Organic Chemistry, University of Barcelona, Barcelona 08028, Spain. enicolas@ub.edu.
⁷ Institut de Biomedicina (IBUB), University of Barcelona, Barcelona 08028, Spain. enicolas@ub.edu.
⁸ Institute for Research in Biomedicine (IRB Barcelona), Barcelona 08028, Spain. falbericio@yachaytech.edu.ec.
⁹ Deparment of Organic Chemistry, University of Barcelona, Barcelona 08028, Spain. falbericio@yachaytech.edu.ec.
¹⁰ CIBER-BBN, Barcelona 08028, Spain. falbericio@yachaytech.edu.ec.
¹¹ School of Chemistry, University of KwaZulu-Natal, Durban 4000, South Africa. falbericio@yachaytech.edu.ec.
¹² School of Chemistry, Yachay Tech, Yachay City of Knowledge, Urcuqui 100119, Ecuador. falbericio@yachaytech.edu.ec.

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Bis(Chloromethyl) Ether / chemistry*
Models, Chemical
Models, Molecular
Molecular Structure
Polycyclic Aromatic Hydrocarbons / chemistry*
Titanium / chemistry*

Substances

Polycyclic Aromatic Hydrocarbons
Bis(Chloromethyl) Ether
titanium tetrachloride
Titanium