Layered Double Hydroxide-Supported Gold Catalyst for Three-Component Aldehyde-Amine-Alkyne Coupling

Abstract

A three-component coupling of aldehydes, amines and an alkyne to generate propargylic amines in nearly quantitative yields, using a layered double hydroxide-supported gold (LDH-AuCl₄) catalyst is described. Both aromatic and aliphatic aldehydes and amines are used for the reaction. No additional co-catalyst or activator is required.

layered double hydroxides - gold - coupling reaction - propargylic amines - heterogeneous catalysis

References

<A NAME="RD13905ST-1">1</A>

Current address: 1311 Gilman Hall, Department of Chemistry, Iowa State University, Ames, IA 50011, USA.

<A NAME="RD13905ST-2A">2a</A> Armstrong RW. Combs AP. Tempst PA. Brown SD. Keating TA. Acc. Chem. Res.  1996,  29:  123 

<A NAME="RD13905ST-2B">2b</A> Ugi I. Domling A. Werner B. J. Heterocycl. Chem.  2000,  37:  647 

<A NAME="RD13905ST-2C">2c</A> Weber L. Illgen K. Almstetter M. Synlett  1999,  366 

<A NAME="RD13905ST-3A">3a</A> Kamijo S. Yamamoto Y. J. Am. Chem. Soc.  2002,  124:  11940 

<A NAME="RD13905ST-3B">3b</A> Domling A. Ugi I. Angew. Chem.  2000,  112:  3300 

<A NAME="RD13905ST-3C">3c</A> Cao C. Shi Y. Odom AL. J. Am. Chem. Soc.  2003,  125:  2880 

<A NAME="RD13905ST-4">4</A> Wei C. Zhang L. Li CJ. Synlett  2004,  1472 

<A NAME="RD13905ST-5A">5a</A> Naota I. Takaya H. Murahashi SI. Chem. Rev.  1998,  98:  2599 

<A NAME="RD13905ST-5B">5b</A> Dyker G. Angew. Chem.  1999,  38:  1698 

<A NAME="RD13905ST-6">6</A> Wei CM. Li Z. Li CJ. Org. Lett.  2003,  5:  4473 ; and references cited therein

<A NAME="RD13905ST-7">7</A> Wei CM. Li CJ. J. Am. Chem. Soc.  2003,  125:  9584 

<A NAME="RD13905ST-8A">8a</A> Kabalka GW. Wang L. Pagni RM. Synlett  2001,  676 

<A NAME="RD13905ST-8B">8b</A> Shi L. Tu YQ. Wang M. Zhang FM. Fan CA. Org. Lett.  2004,  6:  1001 

<A NAME="RD13905ST-8C">8c</A> Gommermann N. Koradin C. Polborn K. Knochel P. Angew. Chem. Int. Ed.  2003,  42:  5763 

<A NAME="RD13905ST-8D">8d</A> Koradin C. Polborn K. Knochel P. Angew. Chem. Int. Ed.  2002,  41:  2535 

<A NAME="RD13905ST-8E">8e</A> Syeda HZS. Halder R. Karla SS. Das J. Iqbal J. Tetrahedron Lett.  2002,  43:  6485 

<A NAME="RD13905ST-9">9</A> Fischer C. Carreira EM. Org. Lett.  2001,  3:  4319 

<A NAME="RD13905ST-10">10</A> Li CJ. Wei C. Chem. Commun.  2002,  268 

<A NAME="RD13905ST-11">11</A> Zhang L. Wei C. Varma RS. Li C.-J. Tetrahedron Lett.  2004,  45:  2443 

<A NAME="RD13905ST-12">12</A> Choudary BM. Sridhar Ch. Kantam ML. Sreedhar B. Tetrahedron Lett.  2004,  45:  7319 

<A NAME="RD13905ST-13A">13a</A> Vos DE. Vankelecom IFK. Jacobs PA. Chiral Catalyst Immobilization and Recycling   Wiley-VCH; Weinheim: 2000. 

<A NAME="RD13905ST-13B">13b</A> Inaki Y. Kajita Y. Hisao H. Yoshida K. Ito K. Hattori T. Chem. Commun.  2001,  2358 

<A NAME="RD13905ST-14">14</A> Cavani F. Trifiro F. Vaccari A. Catal. Today  1991,  11:  173 

<A NAME="RD13905ST-15A">15a</A> Trifiro F. Vaccari A. In Comprehensive Supramolecular Chemistry   Vol. 7:  Alberti G. Bein T. Pergamon; New York: 1996.  p.251 

<A NAME="RD13905ST-15B">15b</A> Sels BF. De Vos D. Jacobs PA. Catal. Rev.  2001,  43:  443 

<A NAME="RD13905ST-16A">16a</A> Sels BF. De Vos DE. Buntinx M. Pierard F. Mesmaeker AK. Jacobs PA. Nature  1999,  400:  855 

<A NAME="RD13905ST-16B">16b</A> Yamaguchi K. Ebitani K. Yoshida T. Yoshida H. Kaneda K. J. Am. Chem. Soc.  1999,  121:  4527 

<A NAME="RD13905ST-17A">17a</A> Choudary BM. Bharathi B. Venkat Reddy Ch. Kantam ML. Raghavan KV. Chem. Commun.  2001,  1736 

<A NAME="RD13905ST-17B">17b</A> Choudary BM. Venkat Reddy Ch. Prakash BV. Kantam ML. Sreedhar B. Chem. Commun.  2003,  754 

<A NAME="RD13905ST-17C">17c</A> Choudary BM. Kantam ML. Rahman A. Venkat Reddy Ch. Rao KK. Angew. Chem. Int. Ed.  2001,  40:  763 

<A NAME="RD13905ST-18">18</A> Miyata S. Clays Clay Miner.  1975,  23:  369 

<A NAME="RD13905ST-19">19</A> Sylvestre JP. Kabashin AV. Sacher E. Meunier M. Luong JHT. J. Am. Chem. Soc.  2004,  126:  7176