Pd(N,N-Dimethyl β-alaninate)2 as a High-Turnover-Number, Phosphine-Free Catalyst for the Suzuki Reaction

Xin Cui; Tian Qin; Jia-Rui Wang; Lei Liu; Qing-Xiang Guo

doi:10.1055/s-2007-965883

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synthesis 2007(3): 393-399
DOI: 10.1055/s-2007-965883

PAPER

Pd(N,N-Dimethyl β-alaninate)₂ as a High-Turnover-Number, Phosphine-Free Catalyst for the Suzuki Reaction

Xin Cui, Tian Qin, Jia-Rui Wang, Lei Liu*, Qing-Xiang Guo*
Department of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. of China
e-Mail: leiliu@ustc.edu; e-Mail: qxguo@ustc.edu.cn;

Further Information

Publication History

Received 25 August 2006
Publication Date:
12 January 2007 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

A novel crystalline, air- and moisture-stable Pd salt, Pd(N,N-dimethyl β-alaninate)₂, was synthesized. This salt was demonstrated to constitute a low-priced, phosphine-free, yet high-turnover-number (TON = 10⁴) catalyst for the Suzuki reactions of various aryl bromides and iodides under mild and simple reaction conditions. Moreover, it was observed that the presence of an olefin could dramatically hamper the Suzuki reaction.

Key words

palladium - Suzuki reaction - phosphine-free ligand - high-turnover-number catalyst

References

Recent reviews:
1a Suzuki A. Chem. Commun. 2005, 4759

Google Scholar
1b Nicolaou KC. Bulger PG. Sarlah D. Angew. Chem. Int. Ed. 2005, 44: 4442

Google Scholar
1c Bellina F. Carpita A. Rossi R. Synthesis 2004, 2419

Google Scholar
1d Miura M. Angew. Chem. Int. Ed. 2004, 43: 2201

Google Scholar
1e Wang Y.-F. Deng W. Liu L. Guo Q.-X. Chin. J. Org. Chem. 2005, 25: 8

Google Scholar
1f Liang Y. Li J.-H. Chin. J. Org. Chem. 2005, 25: 147

Google Scholar
1g Shao Z.-H. Zhang H.-B. Chin. J. Org. Chem. 2005, 25: 282

Google Scholar
1h Han X.-L. Liu G.-X. Lu X.-Y. Chin. J. Org. Chem. 2005, 25: 1182

Google Scholar
2a Farina V. Adv. Synth. Catal. 2004, 346: 1553

Crossref Google Scholar
2b Phan NTS. Van Der Sluys M. Jones CW. Adv. Synth. Catal. 2006, 348: 609

Crossref Google Scholar
4a Zhang C. Huang J. Trudell ML. Nolan SP. J. Org. Chem. 1999, 64: 3804

Crossref PubMed Google Scholar
4b Gstottmayr CWK. Bohm VPW. Herdtweck E. Grosche M. Herrmann W. Angew. Chem. Int. Ed. 2002, 41: 1363

Crossref PubMed Google Scholar
4c Navarro O. Kelly RA. Nolan SP. J. Am. Chem. Soc. 2003, 125: 16194

Crossref PubMed Google Scholar
5a Tao B. Boykin DW. Tetrahedron Lett. 2002, 43: 4955

Crossref Google Scholar
5b Wang L. Li P.-H. Chin. J. Chem. 2006, 24: 770

Crossref Google Scholar
6a Alonso DA. Najera C. Pacheco MC. Org. Lett. 2000, 2: 1823

Crossref Google Scholar
6b Botella L. Najera C. Angew. Chem. Int. Ed. 2002, 41: 179

Crossref Google Scholar
6c Najera C. Gil-Molto J. Karlstorm S. Falvello LR. Org. Lett. 2003, 5: 1451

Crossref Google Scholar
7a Weissman H. Milstein D. Chem. Commun. 1999, 1901

Crossref Google Scholar
7b Bedford RB. Cazin CS. Chem. Commun. 2001, 1540

Crossref Google Scholar
7c Wu K.-M. Huang C.-A. Peng K.-F. Chen C.-T. Tetrahedron 2005, 61: 9679

Crossref Google Scholar
7d Lai Y.-C. Chen H.-Y. Hung W.-C. Lin C.-C. Hong F.-E. Tetrahedron 2005, 61: 9484

Crossref Google Scholar
8 Grasa GA. Hillier AC. Nolan SP. Org. Lett. 2001, 3: 1077

Crossref PubMed Google Scholar
9a Tao B. Boykin DW. Tetrahedron Lett. 2003, 44: 7993

Crossref Google Scholar
9b Li J.-H. Liu W.-J. Org. Lett. 2004, 6: 2809

Crossref Google Scholar
9c Li J.-H. Liu W.-J. Xie Y.-X. J. Org. Chem. 2005, 70: 5409

Crossref Google Scholar
9d Li J.-H. Liang Y. Wang D.-P. Liu W.-J. Xie Y.-X. Yin D.-L. J. Org. Chem. 2005, 70: 2832

Crossref Google Scholar
9e Zhang L. Cui Y.-C. Acta Chim. Sinica 2005, 63: 924

Crossref Google Scholar
9f Yang Y.-F. Zeng C.-X. Luo M.-F. Li Q.-L. Huang C.-B. Acta Chim. Sinica 2005, 63: 1469

Crossref Google Scholar
9g Yi H. Liu JB. Li Q. Tang J. Chin. Chem. Lett. 2005, 16: 1173

Crossref Google Scholar
9h Cui Y.-C. Zhao X.-W. Zhang J.-W. Zhang L. Liu X.-M. Acta Chim. Sinica 2006, 64: 42

Crossref Google Scholar
9i Xie Y.-X. Li J.-H. Yin D.-L. Chin. J. Org. Chem. 2006, 26: 1155

Crossref Google Scholar
9j Yang Y.-F. Zhuang M. Zeng C.-X. Huang C.-B. Luo M.-F. Chin. J. Chem. 2006, 24: 1309

Crossref Google Scholar
10 Najera C. Gil-Molto J. Karlstrom S. Adv. Synth. Catal. 2004, 346: 1798

Crossref Google Scholar
11a Mino T. Shirae Y. Sakamoto M. Fujita T. Synlett 2003, 882

Crossref Google Scholar
11b Mino T. Shirae Y. Sakamoto M. Fujita T. J. Org. Chem. 2005, 70: 2191

Crossref Google Scholar
12 Mukherjee A. Sarkar A. Tetrahedron Lett. 2005, 46: 15

Crossref Google Scholar
13a Liu L. Zhang Y. Wang Y. J. Org. Chem. 2005, 70: 6122

Crossref Google Scholar
13b Xin B. Zhang Y. Cheng K. J. Org. Chem. 2006, 71: 5725

Crossref Google Scholar
14 Deng W. Liu L. Zhang C. Liu M. Guo Q.-X. Tetrahedron Lett. 2005, 46: 7295

Crossref Google Scholar
15 Cui X. Li Z. Tao C.-Z. Xu Y. Li J. Liu L. Guo Q.-X. Org. Lett. 2006, 8: 2467

Crossref PubMed Google Scholar
For some recent examples, see:
16a Gossage RA. Jenkins HA. Yadav PN. Tetrahedron Lett. 2004, 45: 7689

Crossref Google Scholar
16b Dai M. Liang B. Wang C. You Z. Xiang J. Dong G. Chen J. Yang Z. Adv. Synth. Catal. 2004, 346: 1669

Crossref Google Scholar
16c Lee S. J. Organomet. Chem. 2006, 691: 1347

Crossref Google Scholar
17a Miyaura N. Suzuki A. Chem. Rev. 1995, 95: 2457

Google Scholar
17b Nakamura I. Yamamoto Y. Chem. Rev. 2004, 104: 2127

Google Scholar
18 Xu N. Wang Q.-R. Tao F.-G. Chin. J. Org. Chem. 2005, 25: 458

Google Scholar
19 Zou Y. Wang Q.-R. Tao F.-G. Ding Z.-B. Chin. J. Chem. 2004, 22: 215

Google Scholar
20 Li J.-F. Bai G. Lin P.-H. Tian M.-L. Dong C. Li D.-X. Chem. Res. Chin. Univ. 2004, 20: 216

Google Scholar
21 Enokido T. Fugami K. Endo M. Kameyama M. Kosugi M. Adv. Synth. Catal. 2004, 346: 1685

Crossref Google Scholar
22 Denmark SE. Ober MH. Org. Lett. 2003, 5: 1357

Crossref Google Scholar
23 Dai M.-J. Liang B. Wang C.-H. Chen J.-H. Yang Z. Org. Lett. 2003, 6: 221

Google Scholar
24 Riggleman S. DeShong P. J. Org. Chem. 2003, 68: 8106

Crossref Google Scholar
25 Arvela RK. Leadbeater NE. Org. Lett. 2005, 7: 2101

Crossref PubMed Google Scholar

3

Practically speaking, any catalyst displaying a turnover number (TON) of greater than 10³, i.e. a catalyst that can lead to complete conversion of starting materials at a load of 0.1% mol, will be considered as a high-turnover-number catalyst.