A Facile Route to Sterically Hindered and Non-Hindered 4′-Aryl-2,2′:6′,2′′-Terpyridines

Abstract

A facile one-pot synthesis of 4′-aryl-2,2′:6′,2′′-terpyridines from aryl aldehydes and 2-acetylpyridine is presented. The synthesis of terpyridines incorporating sterically hindered aryl groups, such as the 9-anthryl group, can also be readily synthesized using this method.

nitrogen ligands - heterocycles - substituted terpyridines - one-pot reactions

References

<A NAME="RS01605ST-1A">1a</A> Demas JM. DeGra BA. Coord. Chem. Rev.  2001,  211:  317 

<A NAME="RS01605ST-1B">1b</A> For a recent example: Kimura M. Takahashi A. Sakata T. Tsukahara K. Bull. Chem. Soc. Jpn.  1998,  71:  1839 

<A NAME="RS01605ST-1C">1c</A> Péchy P. Rotzinger FP. Nazeeruddin MK. Kohle O. Zakeeruddin SM. Humphry-Baker R. Grätzel M. J. Chem. Soc., Chem. Commun.  1995,  65 

<A NAME="RS01605ST-1D">1d</A> Baldo MA. Thompson ME. Forrest SR. Nature  2000,  403:  750 

<A NAME="RS01605ST-1E">1e</A> Ziessel RJ. Inclusion Phenom. Macrocyclic Chem.  1999,  35:  369 

<A NAME="RS01605ST-2">2</A> Constable EC. Cargill Thompson AMW. Tocher DA. Daniels MAM. New J. Chem.  1992,  16:  855 

<A NAME="RS01605ST-3">3</A> Sauvage J.-P. Collin J.-P. Chambron J.-C. Guillerez S. Coudret C. Balzani V. Barigelletti F. De Cola L. Flamigni L. Chem. Rev.  1994,  94:  993 

<A NAME="RS01605ST-4A">4a</A> Maestri M. Armaroli N. Balzani V. Constable EC. Cargill Thompson AMW. Inorg. Chem.  1995,  34:  2759 

<A NAME="RS01605ST-4B">4b</A> Hammarström L. Barigelletti F. Flamigni L. Indelli MT. Armaroli N. Calogero G. Guardigli M. Sour A. Collin J.-P. Sauvage J.-P. J. Phys. Chem. A  1997,  101:  9061 

<A NAME="RS01605ST-4C">4c</A> Albano G. Balzani V. Constable EC. Maestri M. Smith DR. Inorg. Chim. Acta  1998,  277:  225 

<A NAME="RS01605ST-5">5</A> Mutai T. Cheon J.-D. Arita S. Araki K. J. Chem. Soc., Perkin Trans. 2  2001,  1045 

<A NAME="RS01605ST-6">6</A> Goodall W. Williams JAG. Chem. Commun.  2001,  2514 

<A NAME="RS01605ST-7">7</A> Roberto D. Tessore F. Ugo R. Bruni S. Manfredi A. Quici S. Chem. Commun.  2002,  846 

<A NAME="RS01605ST-8">8</A> Alcock NW. Barker PR. Haider JM. Hannon MJ. Painting CL. Pikramenou Z. Plummer EA. Rissanen K. Saarenketo P. J. Chem. Soc., Dalton Trans.  2000,  1447 

<A NAME="RS01605ST-9">9</A> A comprehensive review of methods up to 1995 is provided by: Cargill Thompson AMW. Coord. Chem. Rev.  1997,  160:  1 

<A NAME="RS01605ST-10A">10a</A> Kröhnke F. Synthesis  1976,  1 

<A NAME="RS01605ST-10B">10b</A> Constable EC. Ward MD. Corr S. Inorg. Chim. Acta  1988,  141:  201 

<A NAME="RS01605ST-10C">10c</A> Frank RL. Riener EF. J. Am. Chem. Soc.  1950,  72:  4182 

<A NAME="RS01605ST-10D">10d</A> Korall P. Börje A. Norrby P.-O. Åkermark B. Acta Chem. Scand.  1997,  51:  760 

<A NAME="RS01605ST-10E">10e</A> Cave GWV. Raston CL. Chem. Commun.  2000,  2199 

<A NAME="RS01605ST-11A">11a</A> Cardenas DJ. Sauvage J.-P. Synlett  1996,  916 

<A NAME="RS01605ST-11B">11b</A> Hanan GS. Schubert US. Volkmer D. Riviere E. Lehn J.-M. Kyritsakas N. Fisher J. Can. J. Chem.  1997,  75:  169 

<A NAME="RS01605ST-11C">11c</A> Fallahpour R.-A. Neuberger M. Zehnder M. New J. Chem.  1999,  23:  53 

<A NAME="RS01605ST-11D">11d</A> Fallahpour R.-A. Eur. J. Inorg. Chem.  1998,  1205 

<A NAME="RS01605ST-12">12</A> Goodall W. Wild K. Arm KJ. Williams JAG. J. Chem. Soc., Perkin Trans. 2  2002,  1669 

<A NAME="RS01605ST-13">13</A> During the preparation of this paper, a similar approach to synthesize 4′-p-tolyl-2,2′:6′,2′′-terpyridine was reported: Vaduvescu S. Potvin PG. Eur. J. Inorg. Chem.  2004,  1763 

<A NAME="RS01605ST-14">14</A> Collin J.-P. Guillerez S. Sauvage J.-P. Barigelletti F. De Cola L. Flamigni L. Balzani V. Inorg. Chem.  1991,  30:  4230 

<A NAME="RS01605ST-15">15</A>

Most of the starting aryl aldehydes were purchased from Aldrich. Aldehydes that were not commercial available were synthesized from the corresponding aryl bromides by lithiation and then formylation with dimethylformamide.

<A NAME="RS01605ST-16">16</A> Wang J. Hanan GS. Loiseau F. Campagna S. Chem. Commun.  2004,  2068 

<A NAME="RS01605ST-17">17</A> Yoo D.-W. Yoo S.-K. Kim C. Lee J.-K. J. Chem. Soc., Dalton Trans.  2002,  3931 

<A NAME="RS01605ST-18">18</A> Michalec JF. Bejune SA. Cuttell DG. Summerton GC. Gertenbach JA. Field JS. Haines RJ. McMillin DR. Inorg. Chem.  2001,  40:  2193 

<A NAME="RS01605ST-19">19</A> Husson J. Beley M. Kirsch G. Tetrahedron Lett.  2003,  44:  1767 

<A NAME="RS01605ST-20">20</A> Persaud L. Barbiero G. Can. J. Chem.  1991,  69:  315