Recyclable Catalysts for Suzuki-Miyaura
Cross-Coupling Reactions at Ambient Temperature Based
on a Simple Merrifield Resin Supported Phenanthroline-Palladium(II)
Complex

Jin Yang; Pinhua Li; Lei Wang

doi:10.1055/s-0030-1258472

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Synthesis 2011(8): 1295-1301
DOI: 10.1055/s-0030-1258472

PAPER

Recyclable Catalysts for Suzuki-Miyaura Cross-Coupling Reactions at Ambient Temperature Based on a Simple Merrifield Resin Supported Phenanthroline-Palladium(II) Complex

Jin Yang^a, Pinhua Li^a, Lei Wang*^a,b
^a Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, P. R. of China
^b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
Fax: +86(561)3090518; e-Mail: leiwang@chnu.edu.cn;

Weitere Informationen

Publikationsverlauf

Received 7 January 2011
Publikationsdatum:
10. März 2011 (online)

Abstract
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Abstract

A novel Merrifield resin immobilized phenanthroline-palladium(II) complex has been developed and was found to be an efficient catalyst for Suzuki-Miyaura cross-coupling reaction between arylboronic acids and a range of aryl halides under mild reaction conditions. The catalyst exhibited both high catalytic activity and stability for Suzuki-Miyaura reaction. Furthermore, the catalyst could be recycled at least 10 times without a significant loss of catalytic activity.

Key words

immobilized catalyst - phenanthroline-palladium(II) complex - Suzuki-Miyaura reaction - recyclability

References

For recent reviews, see:
1a Miyaura N. Suzuki A. Chem. Rev. 1995, 95: 2457

Suche in Google Scholar
1b Miyaura N. Top. Curr. Chem. 2002, 219: 11

Suche in Google Scholar
1c Corbet J.-P. Mignani G. Chem. Rev. 2006, 106: 2651

Suche in Google Scholar
1d Yin L. Liebscher J. Chem. Rev. 2007, 107: 133

Suche in Google Scholar
1e Molander GA. Ellis N. Acc. Chem. Res. 2007, 40: 275

Suche in Google Scholar
1f Martin R. Buchwald SL. Acc. Chem. Res. 2008, 41: 1461

Suche in Google Scholar
1g Alonso F. Beletskaya IP. Yus M. Tetrahedron 2008, 64: 3047

Suche in Google Scholar
2a Suzuki A. Modern Arene Chemistry, In The Suzuki Reaction with Arylboron Compounds in Arene Chemistry Wiley-VCH; Weinheim: 2002. p.53-106
2b Billingsley KL. Buchwald SL. Angew. Chem. Int. Ed. 2008, 47: 4695

Suche in Google Scholar
2c Suzuki K. Sawaki T. Hori Y. Kobayashi T. Synlett 2008, 1809
2d Bellina F. Carpita A. Rossi R. Synthesis 2004, 2419
3a Old DW. Wolfe JP. Buchwald SL. J. Am. Chem. Soc. 1998, 120: 9722

Suche in Google Scholar
3b Wolfe JP. Buchwald SL. Angew. Chem. Int. Ed. 1999, 38: 2413

Suche in Google Scholar
3c Fujihara T. Yoshida S. Ohta H. Tsuji Y. Angew. Chem. Int. Ed. 2008, 47: 8310

Suche in Google Scholar
3d Fujihara T. Yoshida S. Terao J. Tsuji Y. Org. Lett. 2009, 11: 2121

Suche in Google Scholar
4a Mubofu EB. Clark JH. Macquarrie D. Green Chem. 2001, 3: 23

Suche in Google Scholar
4b Rosario-Amorin D. Wang X. Gaboyard M. Clérac R. Nlate S. Heuzé K. Chem. Eur. J. 2009, 15: 12636

Suche in Google Scholar
5a Leadbeater NE. Marco M. Chem. Rev. 2002, 102: 3217

Suche in Google Scholar
5b Yin L. Liebscher J. Chem. Rev. 2007, 107: 133

Suche in Google Scholar
6a Beletskaya IP. Cheprakov AV. Chem. Rev. 2000, 100: 3009

Suche in Google Scholar
6b Gent JP. Savignac MJ. J. Organomet. Chem. 1999, 576: 305

Suche in Google Scholar
7a Yu K. Sommer W. Weck M. Jones CW. J. Catal. 2004, 226: 101

Suche in Google Scholar
7b Yu K. Sommer W. Richardson JM. Weck M. Jones CW. Adv. Synth. Catal. 2005, 347: 161

Suche in Google Scholar
7c Koushik D. Krishanu S. Dipankar S. Subrata KS. Pabitra C. Asim B. Dalton Trans. 2010, 39: 6395

Suche in Google Scholar
8a Bedioui F. Coord. Chem. Rev. 1995, 144: 39

Suche in Google Scholar
8b Li C. Catal. Rev. 2004, 46: 419

Suche in Google Scholar
8c Asefa T. MacLachlan MJ. Coombs N. Ozin GA. Nature 1999, 402: 867

Suche in Google Scholar
8d Crudden CM. Sateesh M. Lewis R. J. Am. Chem. Soc. 2005, 127: 10045

Suche in Google Scholar
8e Karimi B. Abedi S. Clark JH. Budarin V. Angew. Chem. Int. Ed. 2006, 45: 4776

Suche in Google Scholar
8f Huang J. Zhu F. He W. Zhang F. Wang W. Li H. J. Am. Chem. Soc. 2010, 132: 1494

Suche in Google Scholar
8g Shi S. Zhang Y. Green Chem. 2008, 10: 868

Suche in Google Scholar
9a Uozumi Y. Danjo H. Hayashi T. J. Org. Chem. 1999, 64: 3384

Suche in Google Scholar
9b Uozumi Y. Nakai Y. Org. Lett. 2002, 4: 2997

Suche in Google Scholar
9c Yamada YMA. Takeda K. Takahashi H. Ikegami S. J. Org. Chem. 2003, 68: 7733

Suche in Google Scholar
9d Yamada YMA. Takeda K. Takahashi H. Ikegami S. Org. Lett. 2002, 4: 3371

Suche in Google Scholar
9e Fan QH. Ren CY. Yeung CH. Hu WH. Chan ASC. J. Am. Chem. Soc. 1999, 121: 7407

Suche in Google Scholar
9f Ohkuma T. Takeno H. Honda Y. Noyori R. Adv. Synth. Catal. 2001, 343: 369

Suche in Google Scholar
9g Schweizer SP. Becht JM. Drian CL. Tetrahedron 2010, 66: 765

Suche in Google Scholar
9h Luo CC. Zhang YH. Wang YG. J. Mol. Catal. A: Chem. 2005, 229: 7

Suche in Google Scholar
10a Rosario-Amorin D. Wang X. Gaboyard M. Clerac R. Nlate S. Heuz K. Chem. Eur. J. 2009, 15: 12636

Suche in Google Scholar
10b Che C. Li Z. Lin SY. Chen JW. Zheng J. Wu JC. Zheng QX. Zhang GQ. Yang Z. Jiang BW. Chem. Commun. 2009, 5990
10c Gleeson O. Tekoriute R. Gunko YK. Connon SJ. Chem. Eur. J. 2009, 15: 5669

Suche in Google Scholar
10d Wittmann S. Schatz A. Grass RN. Stark WJ. Reiser O. Angew. Chem. Int. Ed. 2010, 49: 1867

Suche in Google Scholar
10e Jin MJ. Lee DH. Angew. Chem. Int. Ed. 2010, 49: 1119

Suche in Google Scholar
11a Bellina F. Carpita A. Rossi R. Synthesis 2004, 2419
11b Tao B. Boykin DW. Tetrahedron Lett. 2003, 44: 7993

Suche in Google Scholar
11c Tao B. Boykin DW. J. Org. Chem. 2004, 69: 4330

Suche in Google Scholar
11d Li JH. Liu WJ. Org. Lett. 2004, 6: 2809

Suche in Google Scholar
11e Li SH. Lin YJ. Cao JG. Zhang SB. J. Org. Chem. 2007, 72: 4067

Suche in Google Scholar
12a Leadbeater NE. Marco M. Chem. Rev. 2002, 102: 3217

Suche in Google Scholar
12b McNamara CA. Dixon MJ. Bradley M. Chem. Rev. 2002, 102: 3275

Suche in Google Scholar
12c Fu GC. Acc. Chem. Res. 2008, 41: 1555

Suche in Google Scholar
12d Surry DS. Buchwald SL. Angew. Chem. Int. Ed. 2008, 47: 6338

Suche in Google Scholar
12e Wang L. Reis A. Seifert A. Philippi T. Ernst S. Jia M. Thiel WR. Dalton Trans. 2009, 3315
12f Shylesh S. Wang L. Thiel WR. Adv. Synth. Catal. 2010, 352: 425

Suche in Google Scholar
13a Phan NTS. Styring P. Green Chem. 2008, 10: 1055

Suche in Google Scholar
13b So CM. Yeung CC. Lau CP. Kwong FY. J. Org. Chem. 2008, 73: 7803

Suche in Google Scholar
13c Kwong FY. Chan ASC. Synlett 2008, 1440
13d Weng Z. Teo S. Hor TSA. Acc. Chem. Res. 2007, 40: 676

Suche in Google Scholar
13e Dai W.-M. Li YN. Zhang Y. Yue CY. Wu JL. Chem. Eur. J. 2008, 14: 5538

Suche in Google Scholar
13f Teo S. Weng Z. Hor TSA. Organometallics 2006, 25: 1199

Suche in Google Scholar
13g Chiang WY. Hong FE. J. Organomet. Chem. 2009, 694: 1473

Suche in Google Scholar
13h Yu SB. Hu XP. Deng J. Huang JD. Wang DY. Duan ZC. Zheng Z. Tetrahedron Lett. 2008, 49: 1253

Suche in Google Scholar
14 Beletskaya IP. Cheprakov AV. Chem. Rev. 2000, 100: 3009

Suche in Google Scholar
15 Sauvage JP. Acc. Chem. Res. 1990, 23: 319

Crossref Suche in Google Scholar
16a Do H.-Q. Kashif Khan RM. Daugulis O. J. Am. Chem. Soc. 2008, 130: 15185

Suche in Google Scholar
16b Qiu J.-W. Zhang X.-G. Tang R.-Y. Zhong P. Li J.-H. Adv. Synth. Catal. 2009, 351: 2319

Suche in Google Scholar
16c Lv X. Liu Y. Qian W. Bao W. Adv. Synth. Catal. 2008, 350: 2507

Suche in Google Scholar
For selected examples, see:
17a Chen W. Li P. Wang L. Tetrahedron 2011, 67: 318

Suche in Google Scholar
17b Wang Z. Yan J. Zhang X. Wang L. Synthesis 2009, 3744
17c Wang M. Li P. Wang L. Eur. J. Org. Chem. 2008, 2255
17d Li P. Wang L. Zhang Y. Wang M. Tetrahedron Lett. 2008, 49: 6650

Suche in Google Scholar
17e Li P. Wang L. Zhang Y. Tetrahedron 2008, 64: 10825

Suche in Google Scholar
18 Deroo S. Defrancq E. Moucheron C. Kirsch-De Mesmaeker A. Dumy P. Tetrahedron Lett. 2003, 44: 8379

Crossref Suche in Google Scholar
19 Mino T. Shirae Y. Sakamoto M. Fujita T. J. Org. Chem. 2005, 70: 2191

Crossref Suche in Google Scholar
20 Zhou W.-J. Wang K.-H. Wang J.-X. Gao Z.-R. Tetrahedron 2010, 66: 7633

Crossref Suche in Google Scholar
21 Bolliger JL. Frech CM. Chem. Eur. J. 2010, 16: 4075

Crossref Suche in Google Scholar
22 Scheuermann GM. Rumi L. Steurer P. Bannwarth W. Mulhaupt R. J. Am. Chem. Soc. 2009, 131: 8262

Crossref Suche in Google Scholar
23 Denmark SE. Ober MH. Org. Lett. 2003, 5: 1357

Crossref Suche in Google Scholar
24 Antelo Miguez JM. Adrio LA. Sousa-Pedrares A. Vila JM. Hii KK. J. Org. Chem. 2007, 72: 7771

Crossref PubMed Suche in Google Scholar
25 Moncomble A. Floch PL. Gosmini C. Chem. Eur. J. 2009, 15: 4770

Crossref Suche in Google Scholar
26 Cho JK. Najman R. Dean TW. Ichihara O. Muller C. Bradley M. J. Am. Chem. Soc. 2006, 128: 6276

Crossref Suche in Google Scholar