Easy Copper-, Ligand- and Amine-Free Sonogashira Coupling Reaction Catalyzed by Palladium on Carbon at Low Catalyst Loading and by Exposure to Air

Guolin Zhang

doi:10.1055/s-2005-863720

LETTER

Easy Copper-, Ligand- and Amine-Free Sonogashira Coupling Reaction Catalyzed by Palladium on Carbon at Low Catalyst Loading and by Exposure to Air

Guolin Zhang*
Department of Medicinal Chemistry, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310031, P. R. China
Fax: +86(571)87217412; e-Mail: guolinzhang@zju.edu.cn;

Abstract

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Abstract

An easy copper-, ligand and amine-free Sonogashira coupling reaction catalyzed by commercially available palladium on carbon with air at low catalyst loading (0.2 mol% Pd) has been developed. Aryl iodides coupled with aromatic alkynes gave good to excellent yields and with aliphatic alkyne gave moderate to good yields. The reaction system is easy to handle.

Key words

Sonogashira coupling - palladium - catalysis - heterogeneous

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References

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

1b Moore JS. Acc. Chem. Res. 1997, 30: 402

1c Sonogashira K. J. Organomet. Chem. 2002, 653: 46

1d Tykwinski RR. Angew. Chem. Int. Ed. 2003, 42: 1566

1e Negishi EJ. Anastasia L. Chem. Rev. 2003, 103: 1979

2a Graham AE. Mckerrecher D. Davies DH. Taylor RJK. Tetrahedron Lett. 1996, 37: 7445

2b Miller MW. Johnson CR. J. Org. Chem. 1997, 62: 1582

2c Sakai A. Aoyama T. Shioiri T. Tetrahedron Lett. 1999, 40: 4211

2d Yoshimura F. Kawata S. Hirama M. Tetrahedron Lett. 1999, 40: 8281

2e Toyota M. Komori C. Ihara M. J. Org. Chem. 2000, 65: 7110

2f Paterson I. Davies RD. Marquez R. Angew. Chem. Int. Ed. 2001, 40: 603

3a Nicolaou KC. Dai WM. Angew. Chem., Int. Ed. Engl. 1991, 30: 1387

3b Grissom JW. Gunawardena GU. Klingberg D. Huang D. Tetrahedron 1996, 52: 6453

4a Wu R. Schumm JS. Pearson DL. Tour JM. J. Org. Chem. 1996, 61: 6906

4b Tour JM. Acc. Chem. Res. 2002, 33: 791

4c Bunz UHF. Chem. Rev. 2000, 100: 1605

5 Siemsen P. Livingston RC. Diederich F. Angew. Chem. Int. Ed. 2000, 39: 2632

6a Alami M. Ferri F. Linstrumelle G. Tetrahedron Lett. 1993, 34: 6403

6b Bohm VPW. Herrmann WA. Eur. J. Org. Chem. 2000, 3679

6c Fu X. Zhang S. Yin J. Schumacher DP. Tetrahedron Lett. 2002, 43: 6673

6d Pal M. Parasuraman K. Gupta S. Yeleswarapu KR. Synlett 2002, 1976

6e Mery D. Heuze K. Astruc D. Chem. Commun. 2003, 1934

7 Mori A. Kawashima J. Shimada T. Suguro M. Hirabayashi K. Nishihara Y. Org. Lett. 2000, 2: 2935

8 Alonso DA. Najera C. Pacheco MC. Tetrahedron Lett. 2002, 43: 9365

9 Gelman D. Buchwald SL. Angew. Chem. Int. Ed. 2003, 42: 5993

10 Arques A. Aunon D. Molina P. Tetrahedron Lett. 2004, 45: 4337

11 Cheng J. Sun Y. Wang F. Guo M. Xu J. Pan Y. Zhang Z. J. Org. Chem. 2004, 69: 5428

12 Urgaonkar S. Verkade JG. J. Org. Chem. 2004, 69: 5752

13a Whitcombe NJ. Hii KK. Gibson SE. Tetrahedron 2001, 57: 7449

13b Hagiwara H. Shimizu Y. Hoshi T. Suzuki T. Ando M. Ohkubo K. Yokoyama C. Tetrahedron Lett. 2001, 42: 4349

13c Djakovitch L. Koehler K. J. Am. Chem. Soc. 2001, 123: 5990

13d LeBlond CR. Andrews AT. Sun Y. Sowa JR. Org. Lett. 2001, 3: 1555

13e Sakurai H. Tsukuda T. Hirao T. J. Org. Chem. 2002, 67: 2721

14a De la Rosa MA. Velarde E. Guzman A. Synth. Commun. 1990, 20: 2059

14b Novak Z. Szabo A. Repasi J. Kotschy A. J. Org. Chem. 2003, 68: 3327

Examples of singular Pd/C-catalyzed Sonogashira reactions from ref.^14a are:

15a Potts KT. Horwitz CP. Fessak A. Keshavarz KM. Nash KE. Toscano PJ. J. Am. Chem. Soc. 1993, 115: 10444

15b Bleicher L. Cosford NDP. Synlett 1995, 1115

15c Cosford NDP. Bleicher L. Herbaut A. McCallum JS. Vernier J. Dawson H. Whitten JP. Adams P. Chavez-Noriega L. Correa LD. Crona JH. Mahaffy LS. Menzaghi F. Rao TR. Reid R. Sacaan AI. Santori E. Stauderman KA. Whelan K. Lloyd GK. McDonald IA. J. Med. Chem. 1996, 39: 3235

15d Bleicher LS. Cosford NDP. Herbaut A. McCallum JS. McDonald IA. J. Org. Chem. 1998, 63: 1109

15e Felpin FX. Vo-Thanh G. Villieras J. Lebreton J. Tetrahedron: Asymmetry 2001, 12: 1121

15f Bates RW. Boonsombat J. J. Chem. Soc., Perkin Trans. 1 2001, 654

15g Heidenreich RG. Kohler K. Krauter JGE. Pietsch J. Synlett 2002, 1118

15h Mori Y. Seki M. J. Org. Chem. 2003, 68: 1571

16 Elangovan A. Wang YH. Ho TI. Org. Lett. 2003, 5: 1841

17 Ma Y. Song C. Jiang W. Wu Q. Wang Y. Liu X. Andrus MB. Org. Lett. 2003, 5: 3317