Ligand-Free Copper Oxide Nanoparticle-Catalyzed
Sonogashira Coupling Reaction

Yu Yuan; Haitao Zhu; Dongbo Zhao; Li Zhang

doi:10.1055/s-0030-1260023

PAPER

Ligand-Free Copper Oxide Nanoparticle-Catalyzed Sonogashira Coupling Reaction

Yu Yuan*^a, Haitao Zhu^a, Dongbo Zhao*^b, Li Zhang^a
^a College of Chemistry & Chemical Engineering, Yangzhou University, Jiangsu Province 225002, P. R. of China
e-Mail: yyuan@yzu.edu.cn;
^b Bayer Technology & Engineering (Shanghai) Co., Ltd., F3 Area, Mu Hua Road, Shanghai Chemical Industry Park, Shanghai 201507, P. R. of China
Fax: +82(21)67120397; e-Mail: tony.zhao@bayertechnology.com;

Abstract

Alle Artikel dieser Rubrik

Abstract

The catalytic Sonogashira coupling reaction of terminal alkynes and aryl halides is developed using copper(II) oxide nanoparticles as catalyst in dimethyl sulfoxide. The procedure is experimentally simple, general, efficient, and free from addition of external cocatalysts or chelating ligands.

Key words

copper(II) oxide nanoparticles - Sonogashira coupling - ligand-free - nano catalyst

Volltext

Referenzen

References

1a Sonogashira K. Tohda Y. Hagihara N. Tetrahedron Lett. 1975, 50: 4467

1b Sonogashira K. In Metal-Catalyzed Cross-Coupling Reactions Diederich F. Stang PJ. Wiley-VCH; Weinheim: 1998. p.203

1c Sonogashira K. In Handbook of Organopalladium Chemistry for Organic Synthesis Negishi E.-I. de Meijere A. Wiley-VCH; New York: 2002. p.493

1d Doucet H. Hierso JC. Angew. Chem. Int. Ed. 2007, 46: 834

1e Chinchilla R. Nájera C. Chem. Rev. 2007, 107: 874

1f Beccalli EM. Broggini G. Martinelli M. Sottocornola S. Chem. Rev. 2007, 107: 5318

1g Alberico D. Scott ME. Lautens M. Chem. Rev. 2007, 107: 174

2a Soler R. Cacchi S. Fabrizi G. Forte G. Martín L. Martínez S. Molins E. Moreno-Mañas M. Petrucci F. Roig A. Sebastián RM. Vallribera A. Synthesis 2007, 3068

2b Gu S.-J. Chen W.-Z. Organometallics 2009, 28: 909

2c Komáromi A. Tolnai GL. Novák Z. Tetrahedron Lett. 2008, 49: 7294

2d Thathagar MB. Kooyman PJ. Boerleider R. Jansen E. Elsevier CJ. Rothenberg G. Adv. Synth. Catal. 2005, 347: 1965

2e Bolligera JL. Frech CM. Adv. Synth. Catal. 2009, 351: 891

2f Mao J.-C. Wu M.-Y. Xie G.-L. Ji S.-J. Adv. Synth. Catal. 2009, 351: 2101

2g Sedelmeier J. Ley SV. Lange H. Baxendale IR. Eur. J. Org. Chem. 2009, 4412

2h Li J.-H. Liang Y. Xie Y.-X. J. Org. Chem. 2005, 70: 4393

2i Fabrizi G. Goggiamani A. Sferrazza A. Cacchi S. Angew. Chem. Int. Ed. 2010, 49: 1

2j Carpita A. Ribecai A. Tetrahedron Lett. 2009, 50: 204

2k Wang L. Li P.-H. Chin. J. Chem. 2003, 14: 474 ; Chem. Abstr. 2003, 139, 179825

3a Okuro K. Furuune M. Enna M. Miura M. Nomura M. J. Org. Chem. 1993, 58: 4716

3b Wang L. Li P.-H. Zhang Y.-C. Chem. Commun. 2004, 14

3c Rattan KG. Craig GB. Venkataraman D. Org. Lett. 2001, 3: 4315

3d Saejueng P. Bates CG. Venkataraman D. Synthesis 2005, 1706

3e Ma D.-W. Liu F. Chem. Commun. 2004, 1934

3f Wang YF. Deng W. Liu L. Guo QX. Chin. Chem. Lett. 2005, 16: 1197 ; Chem. Abstr. 2005, 144, 22662

3g Xie Y.-X. Deng C.-L. Pi S.-F. Li J.-H. Yin D.-L. Chin. J. Chem. 2006, 17: 1290 ; Chem. Abstr. 2007, 147, 343735

3h Guo S.-M. Deng C.-L. Li J.-H. Chin. Chem. Lett. 2007, 18: 13 ; Chem. Abstr. 2007, 147, 143082

3i Li J.-H. Li J.-L. Wang D.-P. Pi S.-F. Xie Y.-X. Zhang M.-B. Hu X.-C. J. Org. Chem. 2007, 72: 2053

4a Feng L.-Z. Liu F.-X. Sun P.-P. Bao J.-C. Synlett 2008, 1415

4b Han J. Liu Y. Guo R. J. Am. Chem. Soc. 2009, 131: 2060

4c Bell AT. Science 2003, 299: 1688

4d Lucas E. Decker S. Khaleel A. Seitz A. Fultz S. Ponce A. Li W. Carnes C. Klabunde KJ. Chem. Eur. J. 2001, 7: 2505

4e Schlogl R. Hamid SBA. Angew. Chem. Int. Ed. 2004, 43: 1628

4f Zhang Z.-F. Dong C.-G. Yang C.-H. Hu D. Long J. Wang L. Li H. Chen Y. Kong D. Adv. Synth. Catal. 2010, 352: 1600

4g Kantam ML. Laha S. Yadav J. Choudary BM. Sreedhara B. Adv. Synth. Catal. 2005, 347: 1212

4h Mori K. Hara T. Mizugaki T. Ebitani K. Kaneda K. J. Am. Chem. Soc. 2004, 126: 10657

4i Su F.-Z. Liu Y.-M. Wang L.-C. Cao Y. He H.-Y. Fan K.-N. Angew. Chem. Int. Ed. 2008, 47: 334

4j Karimi B. Abedi S. Clark JH. Budarin V. Angew. Chem. Int. Ed. 2006, 45: 4776

5a Reddy VP. Swapna K. Kumar AV. Rao KR. Synlett 2009, 2783

5b Jammi S. Sakthivel S. Rout L. Mukherjee T. Mandal S. Mitra R. Saha P. Punniyamurthy T. J. Org. Chem. 2009, 74: 1971

5c Rout L. Sen TK. Punniyamurthy T. Angew. Chem. Int. Ed. 2007, 46: 5583

5d Zhang J.-T. Zhang Z.-H. Wang Y. Zheng X.-Q. Wang Z.-Y. Eur. J. Org. Chem. 2008, 5112

5e Rout L. Jammi S. Punniyamurthy T. Org. Lett. 2007, 17: 3397

5f Reddy VP. Kumar AV. Swapna K. Rao KR. Org. Lett. 2009, 4: 951

5g Kantam ML. Yadav J. Laha S. Sreedhar B. Jha S. Adv. Synth. Catal. 2007, 349: 1938

5h Ranu BC. Saha A. Jana R. Adv. Synth. Catal. 2007, 349: 2690

5i Saha P. Ramana T. Purkait N. Ali MA. Paul R. Punniyamurthy T. J. Org. Chem. 2009, 74: 8719

5j Liu Z.-J. Vors JP. Gesing ERF. Bolm C. Adv. Synth. Catal. 2010, 352: 3158

5k Liu Z.-J. Vors JP. Gesing ERF. Bolm C. Green Chem. 2011, 13: 42

5l Correa A. Bolm C. Adv. Synth. Catal. 2007, 349: 2673

6 Pachon LD. Maarseveen JH. Rothenberg G. Adv. Synth. Catal. 2005, 347: 811

7 Tang B.-X. Wang F. Li J.-H. Xie Y.-X. Zhang M.-B. J. Org. Chem. 2007, 72: 6294

8 Thathagar MB. Beckers J. Rothenberg G. Green Chem. 2004, 6: 215

For references on superbase system KOH/DMSO, see:

9a Klusener PAA. Brandsma L. Verkruijsse HD. Schleyer PvR. Friedl T. Pi R. Angew. Chem., Int. Ed. Engl. 1986, 25: 465

9b Brandsma L. Malkina AG. Lochmann L. Schleyer PvR. Recl. Trav. Chim. Pays-Bas 1994, 113: 529

9c Schlosser M. Pure Appl. Chem. 1988, 60: 1627

9d Caubere P. Chem. Rev. 1993, 93: 2317

For the use of superbases in organocatalysis, see:

9e Superbases for Organic Synthesis Ishikawa T. Wiley; West Sussex: 2009.

9f Yuan Y. Thom I. Kim SH. Chen D.-T. Beyer A. Bonnamour J. Zuidema E. Chang S. Bolm C. Adv. Synth. Catal. 2010, 352: 2892

10a Gaikwad AV. Holuigue A. Thathagar MB. Elshof JE. Rothenberg G. Chem. Eur. J. 2007, 13: 6908

10b Pachón LD. Rothenberg G. Appl. Organomet. Chem. 2008, 22: 288