title: Formylation of electron-rich aromatic rings mediated by dichloromethyl methyl ether and TiCl4: scope and limitations.
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.
authors.affiliation: Institute for Research in Biomedicine (IRB Barcelona), Barcelona 08028, Spain. jmbofill@ub.edu.|Deparment of Organic Chemistry, University of Barcelona, Barcelona 08028, Spain. jmbofill@ub.edu.
authors.forename: Iván
authors.initials: I
authors.lastname: Ramos-Tomillero
authors.affiliation: Institute for Research in Biomedicine (IRB Barcelona), Barcelona 08028, Spain. jmbofill@ub.edu.|Deparment of Organic Chemistry, University of Barcelona, Barcelona 08028, Spain. jmbofill@ub.edu.
authors.forename: Marta
authors.initials: M
authors.lastname: Paradís-Bas
authors.affiliation: Department of Physical Chemistry, University of Barcelona, Barcelona 08028, Spain. i.moreira@ub.edu.|Institut de Química Teòrica i Computacional (IQTCUB), University of Barcelona, Barcelona 08028, Spain. i.moreira@ub.edu.
authors.forename: Ibério
authors.initials: I
authors.lastname: de Pinho Ribeiro Moreira
authors.affiliation: Deparment of Organic Chemistry, University of Barcelona, Barcelona 08028, Spain. jmbofill@ub.edu.|Institut de Química Teòrica i Computacional (IQTCUB), University of Barcelona, Barcelona 08028, Spain. jmbofill@ub.edu.
authors.forename: Josep María
authors.initials: JM
authors.lastname: Bofill
authors.affiliation: Deparment of Organic Chemistry, University of Barcelona, Barcelona 08028, Spain. enicolas@ub.edu.|Institut de Biomedicina (IBUB), University of Barcelona, Barcelona 08028, Spain. enicolas@ub.edu.
authors.forename: Ernesto
authors.initials: E
authors.lastname: Nicolás
authors.affiliation: Institute for Research in Biomedicine (IRB Barcelona), Barcelona 08028, Spain. falbericio@yachaytech.edu.ec.|Deparment of Organic Chemistry, University of Barcelona, Barcelona 08028, Spain. falbericio@yachaytech.edu.ec.|CIBER-BBN, Barcelona 08028, Spain. falbericio@yachaytech.edu.ec.|School of Chemistry, University of KwaZulu-Natal, Durban 4000, South Africa. falbericio@yachaytech.edu.ec.|School of Chemistry, Yachay Tech, Yachay City of Knowledge, Urcuqui 100119, Ecuador. falbericio@yachaytech.edu.ec.
authors.forename: Fernando
authors.initials: F
authors.lastname: Albericio
mesh_terms: D001725:Bis(Chloromethyl) Ether / Q000737:chemistry*; D008956:Models, Chemical; D008958:Models, Molecular; D015394:Molecular Structure; D011084:Polycyclic Aromatic Hydrocarbons / Q000737:chemistry*; D014025:Titanium / Q000737:chemistry*
chemical_list: D011084:Polycyclic Aromatic Hydrocarbons; D001725:Bis(Chloromethyl) Ether; C025096:titanium tetrachloride; D014025:Titanium
references.citation: Angew Chem Int Ed Engl. 2012 Sep 10;51(37):9422-4
references.pmid: 22907673
references.citation: J Org Chem. 2005 Mar 18;70(6):2325-8
references.pmid: 15760222
references.citation: Chem Rev. 2009 Jun;109(6):2455-504
references.pmid: 19364121
references.citation: Org Lett. 2005 Sep 1;7(18):3861-4
references.pmid: 16119917
references.citation: J Am Chem Soc. 2011 Oct 26;133(42):16901-10
references.pmid: 21861488
references.citation: Org Lett. 2014 Mar 21;16(6):1772-5
references.pmid: 24617568
references.citation: Org Lett. 2012 Nov 2;14(21):5468-71
references.pmid: 23075145
references.citation: J Org Chem. 2014 Feb 21;79(4):1867-71
references.pmid: 24490660
references.citation: Chem Rev. 2014 Jan 22;114(2):901-26
references.pmid: 24446748
references.citation: J Org Chem. 2013 Apr 5;78(7):3438-44
references.pmid: 23477294
references.citation: Org Lett. 2010 Apr 2;12(7):1552-5
references.pmid: 20192259
references.citation: Mol Microbiol. 2006 Mar;59(6):1664-77
references.pmid: 16553874
references.citation: Molecules. 2013 May 06;18(5):5155-62
references.pmid: 23648593
references.citation: Chem Rev. 1946 Apr;38:227-54
references.pmid: 21024865
references.citation: Angew Chem Int Ed Engl. 2013 Jul 29;52(31):8045-9
references.pmid: 23788412
references.citation: Org Lett. 2012 Nov 2;14(21):5472-5
references.pmid: 23075170