Sterically Demanding, Zwitterionic Trialkylphosphonium Sulfonates as Air-Stable Ligand Precursors for Efficient Palladium-Catalyzed Cross-Couplings of Aryl Bromides and Chlorides

William S. Brown; D’Ariel D. Boykin; M. Quentin Sonnier Jr; William D. Clark; Fallon V. Brown; Kevin H. Shaughnessy

doi:10.1055/s-2008-1067095

SPECIALTOPIC

Sterically Demanding, Zwitterionic Trialkylphosphonium Sulfonates as Air-Stable Ligand Precursors for Efficient Palladium-Catalyzed Cross-Couplings of Aryl Bromides and Chlorides

William S. Brown, D’Ariel D. Boykin, M. Quentin Sonnier, William D. Clark, Fallon V. Brown, Kevin H. Shaughnessy*
Department of Chemistry, The University of Alabama, Tuscaloosa, AL 35487-0336, USA
Fax: +1(205)3489104; e-Mail: kshaughn@bama.ua.edu;

Abstract

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Abstract

3-(Di-tert-butylphosphonium)propane sulfonate (DTBPPS) and 3-(diadamantylphosphonium)propane sulfonate (DAPPS) are air-stable pre-ligands for aqueous-phase palladium-catalyzed cross-coupling reactions. Both DTBPPS and DAPPS were found to give active catalysts for the Sonogashira coupling of aryl bromides at room temperature and 4-chloroanisole at 80 °C. These ligands also gave effective catalysts for the aqueous-phase Suzuki coupling of aryl bromides at room temperature.

Key words

palladium - cross-coupling - ligands - aqueous-phase catalysis - aryl halides

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References

1a Corbet J.-P. Mignani G. Chem. Rev. 2006, 106: 2651

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

2a Hartwig JF. Kawatsura M. Hauck SI. Shaughnessy KH. Alcazar-Roman LM. J. Org. Chem. 1999, 64: 5575

2b Hill LL. Moore LR. Huang R. Craciun R. Vincent AJ. Dixon DA. Chou J. Woltermann CJ. Shaughnessy KH. J. Org. Chem. 2006, 71: 5117

2c Littke AF. Dai C. Fu GC. J. Am. Chem. Soc. 2000, 122: 4020

2d Littke AF. Fu GC. J. Am. Chem. Soc. 2001, 123: 6989

2e Littke AF. Schwarz L. Fu GC. J. Am. Chem. Soc. 2002, 124: 6343

2f Zapf A. Ehrentraut A. Beller M. Angew. Chem. Int. Ed. 2000, 39: 4153

3a Wolfe JP. Singer RA. Yang BH. Buchwald SL. J. Am. Chem. Soc. 1999, 121: 9550

3b Wolfe JP. Tomori H. Sadighi JP. Yin J. Buchwald SL. J. Org. Chem. 2000, 65: 1158

3c Kuwabe S.-I. Torraca KE. Buchwald SL. J. Am. Chem. Soc. 2001, 123: 12202

3d Anderson KW. Tundel RE. Ikawa T. Altman RA. Buchwald SL. Angew. Chem. Int. Ed. 2006, 45: 6523

3e Harkal S. Kumar K. Michalik D. Zapf A. Jackstell R. Rataboul F. Riermeier T. Monsees A. Beller M. Tetrahedron Lett. 2005, 46: 3237

3f Rataboul F. Zapf A. Jackstell R. Harkal S. Reiermeier T. Monsees A. Dingerdissen U. Beller M. Chem. Eur. J. 2004, 10: 2983

4 Anderson KW. Ikawa T. Tundel RE. Buchwald SL. J. Am. Chem. Soc. 2006, 128: 10694

5a Kantchev EAB. O" Brien CJ. Organ MG. Angew. Chem. Int. Ed. 2007, 46: 2768

5b Grasa GA. Viciu MS. Huang J. Nolan SP. J. Org. Chem. 2001, 66: 7729

5c Viciu MS. Germaneau RF. Nolan SP. Org. Lett. 2002, 4: 4053

5d Jørgensen M. Lee S. Liu X. Wolkowski JP. Hartwig JF. J. Am. Chem. Soc. 2002, 124: 12557

5e Gstöttmayr CWK. Böhm VPW. Herdtweck E. Grosche M. Herrmann WA. Angew. Chem. Int. Ed. 2002, 41: 1363

5f Marion N. Navarro O. Mei J. Stevens ED. Scott NM. Nolan SP. J. Am. Chem. Soc. 2006, 128: 4101

6 Garrett CE. Prasad K. Adv. Synth. Catal. 2004, 346: 889

7a Li C.-J. Chem. Rev. 2005, 105: 3095

7b Li C.-J. Chen L. Chem. Soc. Rev. 2006, 35: 68

8 Miyaura N. Yangi T. Suzuki A. Synth. Commun. 1981, 11: 513

9 Casalnuovo AL. Calabrese JC. J. Am. Chem. Soc. 1990, 112: 4324

10a Shaughnessy KH. Eur. J. Org. Chem. 2006, 1827

10b Shaughnessy KH. DeVasher RB. Curr. Org. Chem. 2005, 9: 585

11 DeVasher RB. Spruell JM. Dixon DA. Broker GA. Griffin ST. Rogers RD. Shaughnessy KH. Organometallics 2005, 24: 962

12 DeVasher RB. Moore LR. Shaughnessy KH. J. Org. Chem. 2004, 69: 7919

13a Nishimura M. Ueda M. Miyaura N. Tetrahedron 2002, 58: 5779

13b Konovets A. Penciu A. Framery E. Percina N. Goux-Henry C. Sinou D. Tetrahedron Lett. 2005, 46: 3205

14 Anderson KW. Buchwald SL. Angew. Chem. Int. Ed. 2005, 44: 6175

15 Shaughnessy KH. Booth RS. Org. Lett. 2001, 3: 2757

16 Netherton MR. Fu GC. Org. Lett. 2001, 3: 4295

17 Paetzold E. Kinting A. Oehme G. J. Prakt. Chem. 1987, 329: 725

18 Goerlich JR. Schmutzler R. Phosphorus, Sulfur Silicon Relat. Elem. 1995, 102: 211

19 Wolf C. Lerebours R. Org. Biomol. Chem. 2004, 2: 2161

20 Mino T. Shirae Y. Saito T. Sakamoto M. Fujita T. J. Org. Chem. 2006, 71: 9499

21 Collins CJ. Hanack M. Stutz H. Auchter G. Schoberth W. J. Org. Chem. 1983, 48: 5260

22 Gavryushin A. Kofink C. Manolikakes G. Knochel P. Tetrahedron 2006, 62: 7521