Self-Supported Thiourea-Palladium Complexes: Highly Air-Stable and Recyclable­ Catalysts for the Suzuki Reaction in Neat Water

Wei Chen; Rui Li; Yong Wu; Li-Sheng Ding; Ying-Chun Chen

doi:10.1055/s-2006-942531

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Self-Supported Thiourea-Palladium Complexes: Highly Air-Stable and Recyclable Catalysts for the Suzuki Reaction in Neat Water

Wei Chen^a, Rui Li^b, Yong Wu^a, Li-Sheng Ding^b, Ying-Chun Chen*^a
^a Key Laboratory of Drug-Targeting of Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, P. R. of China
Fax: +86(28)85502609; e-Mail: ycchenhuaxi@yahoo.com.cn;
^b Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, P. R. of China

Abstract

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Abstract

The synthesis of novel self-supported thiourea-PdCl₂ complexes is described. The heterogeneous catalysts exhibited high catalytic activities in the Suzuki coupling reaction of aryl bromides and aryl boronic acids in neat water under aerobic conditions. Moreover, the catalysts could be easily reused without diminishing the catalytic activity.

Key words

thiourea - palladium - self-supported - heterogeneous - Suzuki reaction

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References

For recent reviews on Suzuki coupling, see:

<A NAME="RF06206SS-1A">1a</A> Bai L. Wang J.-X. Curr. Org. Chem. 2005, 9: 535

<A NAME="RF06206SS-1B">1b</A> Miura M. Angew. Chem. Int. Ed. 2004, 43: 2201

<A NAME="RF06206SS-1C">1c</A> Hassan J. Sévignon M. Gozzi C. Schulz E. Lemaire M. Chem. Rev. 2002, 102: 1359

<A NAME="RF06206SS-1D">1d</A> Kotha S. Lahiri K. Kashinath D. Tetrahedron 2002, 58: 9633

<A NAME="RF06206SS-2A">2a</A> Littke AF. Fu GC. Angew. Chem. Int. Ed. 2002, 41: 4176

<A NAME="RF06206SS-2B">2b</A> Fu GC. J. Org. Chem. 2004, 69: 3245 ; and references therein.

<A NAME="RF06206SS-3">3</A> For a review, see: Cole-Hamilton DJ. Science 2003, 299: 1702

For self-supported metal-organic catalysts, see:

<A NAME="RF06206SS-4A">4a</A> Seo JS. Whang D. Lee H. Jun SI. Oh J. Jeon YJ. Kim K. Nature 2000, 404: 982

<A NAME="RF06206SS-4B">4b</A> Takizawa S. Somei H. Jayaprakash D. Sasai H. Angew. Chem. Int. Ed. 2003, 42: 5711

<A NAME="RF06206SS-4C">4c</A> Dai L.-X. Angew. Chem. Int. Ed. 2004, 43: 5726

<A NAME="RF06206SS-4D">4d</A> Ding K. Wang Z. Wang X. Liang Y. Wang X. Chem. Eur. J. 2006, 12: 5188

<A NAME="RF06206SS-4E">4e</A> Liang Y. Jing Q. Li X. Shi L. Ding K. J. Am. Chem. Soc. 2005, 127: 7694

<A NAME="RF06206SS-4F">4f</A> Peng HY. Lam CK. Mak TCW. Cai ZW. Ma WT. Li YX. Wong HNC. J. Am. Chem. Soc. 2005, 127: 9603

<A NAME="RF06206SS-4G">4g</A> Wang X. Wang X. Guo H. Wang Z. Ding K. Chem. Eur. J. 2005, 11: 4078

<A NAME="RF06206SS-4H">4h</A> Wang X. Shi L. Li M. Ding K. Angew. Chem. Int. Ed. 2005, 44: 6362

<A NAME="RF06206SS-4I">4i</A> Wang X. Ding K. J. Am. Chem. Soc. 2004, 126: 10524

<A NAME="RF06206SS-4J">4j</A> Guo H. Wang X. Ding K. Tetrahedron Lett. 2004, 45: 2009

<A NAME="RF06206SS-4K">4k</A> Dorta R. Shimon L. Milstein D. J. Organomet. Chem. 2004, 689: 751

For the cross-linked dendritic or star-shaped catalysts, see:

<A NAME="RF06206SS-5A">5a</A> Reetz MT. Giebel D. Angew. Chem. Int. Ed. 2000, 39: 2498

<A NAME="RF06206SS-5B">5b</A> Rigaut S. Delville M.-H. Losada J. Astruc D. Inorg. Chim. Acta 2002, 334: 225

<A NAME="RF06206SS-5C">5c</A> Harada T. Nakatsugawa M. Synlett 2006, 321

<A NAME="RF06206SS-5D">5d</A> Liu Q.-P. Chen Y.-C. Wu Y. Zhu J. Deng J.-G. Synlett 2006, 1503

<A NAME="RF06206SS-5E">5e</A> For self-supported amphiphilic polymeric Pd catalyst, see: Yamada YMA. Takeda K. Takahashi H. Ikegami S. Org. Lett. 2002, 4: 3371

<A NAME="RF06206SS-6">6</A> Yang D. Chen Y.-C. Zhu N.-Y. Org. Lett. 2004, 6: 1577

For recent work on thiourea-Pd catalysts, see:

<A NAME="RF06206SS-7A">7a</A> Chen W. Li R. Han B. Li B.-J. Chen Y.-C. Wu Y. Ding L.-S. Yang D. Eur. J. Org. Chem. 2006, 1177

<A NAME="RF06206SS-7B">7b</A> Dai M. Liang B. Wang C. Chen J. Yang Z. Org. Lett. 2004, 6: 221

<A NAME="RF06206SS-7C">7c</A> Dai M. Liang B. Wang C. You Z. Xiang J. Dong G. Chen J. Yang Z. Adv. Synth. Catal. 2004, 346: 1669

<A NAME="RF06206SS-7D">7d</A> For furancarbo-thioamide-based palladacycles, see: Xiong Z. Wang N. Dai M. Li A. Chen J. Yang Z. Org. Lett. 2004, 6: 3337

For reviews, see:

<A NAME="RF06206SS-8A">8a</A> Shaughnessy KH. DeVasher RB. Curr. Org. Chem. 2005, 9: 585

<A NAME="RF06206SS-8B">8b</A> Leadbeater NE. Chem. Commun. 2005, 2881

<A NAME="RF06206SS-8C">8c</A> Genêt JP. Savignac M. J. Organomet. Chem. 1999, 576: 305

<A NAME="RF06206SS-8D">8d</A> Joó F. Kathó Á. J. Mol. Catal. A: Chem. 1997, 116: 3

For recent examples of heterogeneous Suzuki reaction in water, see:

<A NAME="RF06206SS-9A">9a</A> Lysen M. Köhler K. Synthesis 2006, 692

<A NAME="RF06206SS-9B">9b</A> Kim J.-H. Kim J.-W. Shokouhimehr M. Lee Y.-S. J. Org. Chem. 2005, 70: 6714

<A NAME="RF06206SS-9C">9c</A> Zhang G. Synthesis 2005, 537

<A NAME="RF06206SS-9D">9d</A> Lu G. Franzén R. Zhang Q. Xu Y. Tetrahedron Lett. 2005, 46: 4255

<A NAME="RF06206SS-9E">9e</A> Lysen M. Köhler K. Synlett 2005, 1671

<A NAME="RF06206SS-9F">9f</A> Uozumi Y. Kikuchi M. Synlett 2005, 1775

Self-Supported Thiourea-Palladium Complexes: Highly Air-Stable and Recyclable­ Catalysts for the Suzuki Reaction in Neat Water

Self-Supported Thiourea-Palladium Complexes: Highly Air-Stable and Recyclable Catalysts for the Suzuki Reaction in Neat Water