Copper- and Palladium-Containing Perovskites: Catalysts for the Ullmann and Sonogashira Reactions

Sophie Lohmann; Stephen P. Andrews; Brenda J. Burke; Martin D. Smith; J. Paul Attfield; Hirohisa Tanaka; Kimiyoshi Kaneko; Steven V. Ley

doi:10.1055/s-2005-865233

LETTER

Copper- and Palladium-Containing Perovskites: Catalysts for the Ullmann and Sonogashira Reactions

Sophie Lohmann^a, Stephen P. Andrews^a, Brenda J. Burke^a, Martin D. Smith^a, J. Paul Attfield^b, Hirohisa Tanaka^c, Kimiyoshi Kaneko^d, Steven V. Ley*^a
^a Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK
Fax: +44(1223)336442; e-Mail: svl1000@cam.ac.uk;
^b School of Chemistry, CSEC, The University of Edinburgh, Erskine Williamson Building, The King’s Buildings, Mayfield Road, Edinburgh, EH9 3JZ, UK
^c Materials R&D Division, Technical Centre, Daihatsu Motor Co. Ltd. Ryuo, Gamo-gun, Shiga 520-2593, Japan
^d Hokko Chemical Industry Co., Ltd., Fine Chemicals Research Laboratories, 2165, Toda, Atsugi-shi, Kanagawa-ken 243-0023, Japan

Abstract

Alle Artikel dieser Rubrik

Abstract

The utility of perovskite-based materials in organic synthesis is explored through examination of a series of copper- and palladium-containing perovskites in Ullmann and Sonogashira type reactions. La_0.9Ce_0.1Co_0.6Cu_0.4O₃ is identified as an effective catalyst for the synthesis of a range of biaryl ether and thioether functionalities, whilst a Cu- and Pd-containing perovskite is effective in the Sonogashira reaction. These results suggest that perovskites may be useful leads in the search for new catalysts and reagents for organic synthesis.

Key words

perovskite - catalyst - Ullmann - cross-coupling - Sonogashira

Volltext

Referenzen

References

<A NAME="RD03505ST-1">1</A> Attfield JP. Int. J. Inorg. Mater. 2001, 3: 1147

<A NAME="RD03505ST-2">2</A> Cava RJ. J. Am. Ceram. Soc. 2000, 83: 5

<A NAME="RD03505ST-3">3</A> Ramirez AP. J. Phys.: Condens. Mat. 1997, 9: 8171

<A NAME="RD03505ST-4">4</A> Nishihata Y. Mizuki J. Akao T. Tanaka H. Uenishi M. Kimura M. Okamoto T. Hamada N. Nature 2002, 418: 164

<A NAME="RD03505ST-5">5</A> Smith MD. Stepan AF. Ramarao C. Brennan PE. Ley SV. Chem. Commun. 2003, 2652

<A NAME="RD03505ST-6">6</A> Andrews SP. Stepan AF. Ley SV. Tanaka H. Smith MD. Adv. Synth. Catal. 2005, in press

<A NAME="RD03505ST-7">7</A> Raveau B. Rao CNR. Transition Metal Oxides: Structure, Properties and Synthesis of Ceramic Oxides John Wiley & Sons; Oxford: 1998.

<A NAME="RD03505ST-8">8</A> Ullmann F. Chem. Ber. 1903, 2389

<A NAME="RD03505ST-9">9</A> Ley SV. Thomas AW. Angew. Chem. Int. Ed. 2003, 42: 5400

<A NAME="RD03505ST-10">10</A> Nelson TD. Crouch RD. Org. React. 2004, 63: 265

<A NAME="RD03505ST-11">11</A> Marcoux JF. Doye S. Buchwald SL. J. Am. Chem. Soc. 1997, 119: 10539

<A NAME="RD03505ST-12">12</A> Kwong FY. Buchwald SL. Org. Lett. 2002, 4: 3517

<A NAME="RD03505ST-13">13</A> Capdevielle P. Maumy M. Tetrahedron Lett. 1993, 34: 1007

<A NAME="RD03505ST-14">14</A> Ma DW. Xia CF. Org. Lett. 2001, 3: 2583

<A NAME="RD03505ST-15">15</A> Ma DW. Zhang YD. Yao JC. Wu SH. Tao FG. J. Am. Chem. Soc. 1998, 120: 12459

<A NAME="RD03505ST-16">16</A> Sonogashira K. Tohda Y. Hagihara N. Tetrahedron Lett. 1975, 4467

<A NAME="RD03505ST-17">17</A> Cassar L. J. Organomet. Chem. 1975, 93: 253

<A NAME="RD03505ST-18">18</A> Dieck HA. Heck FR. J. Organomet. Chem. 1975, 93: 259

<A NAME="RD03505ST-19">19</A> Soheili A. Albaneze-Walker J. Murry JA. Dormer PG. Hughes DL. Org. Lett. 2003, 5: 4191

<A NAME="RD03505ST-20">20</A> Chouzier S. Gruber M. Djakovitch L. J. Mol. Catal. A: Chem. 2004, 212: 43

<A NAME="RD03505ST-21">21</A> Saphier M. Masarwa A. Cohen H. Meyerstein D. Eur. J. Inorg. Chem. 2002, 1226

<A NAME="RD03505ST-22">22</A> Park SB. Alper H. Chem. Commun. 2004, 1306

<A NAME="RD03505ST-23">23</A> Novak Z. Szabo A. Repasi J. Kotschy A. J. Org. Chem. 2003, 68: 3327

<A NAME="RD03505ST-24">24</A> Wang L. Li PH. Zhang YC. Chem. Commun. 2004, 514

<A NAME="RD03505ST-25">25</A> Son SU. Jang Y. Park J. Na HB. Park HM. Yun HJ. Lee J. Hyeon T. J. Am. Chem. Soc. 2004, 126: 5026

<A NAME="RD03505ST-26">26</A> Leadbeater NE. Marco M. Tominack BJ. Org. Lett. 2003, 5: 3919

<A NAME="RD03505ST-27">27</A> Thathagar MB. Beckers J. Rothenberg G. Green Chem. 2004, 6: 215

<A NAME="RD03505ST-28">28</A> Appukkuttan P. Dehaen W. Van der Eycken E. Eur. J. Org. Chem. 2003, 4713