Palladium-Catalyzed Mono-α-arylation of Acetone at Room Temperature

Chemistry - A European Journal

Volumn 21, Issue 31, 2015, Pages 11006-11009

  Macqueen, Preston M ^a   Chisholm, Alicia J ^a   Hargreaves, Breanna K V ^a   Stradiotto, Mark ^a  

^a DALHOUSIE UNIVERSITY   (Canada)

Author keywords

arylation; cross coupling; Josiphos; palladium; room temperature

Indexed keywords

ACETONE; AROMATIC COMPOUNDS; CHLORINE COMPOUNDS; PALLADIUM;

ARYLATIONS; CATALYST SYSTEM; CROSS-COUPLINGS; JOSIPHOS; ORTHO-SUBSTITUTION; PALLADIUM-CATALYZED; PROOF-OF-PRINCIPLE EXPERIMENTS; TRIFLUOROMETHYL;

CHEMICAL REACTIONS;

EID: 84941884445     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201500834     Document Type: Article

References (61)

1. H. C. Shen, in Applications of Transition Metal Catalysis in Drug Discovery and Development: An Industrial Perspective (Eds.:, M.L. Crawley, B.M. Trost,), John Wiley & Sons, Hoboken, NJ (USA), 2012, pp. 25-96;
2. J. Magano, J. R. Dunetz, in New Trends in Cross-Coupling: Theory and Application (Ed.:, T.J. Colacot,), Royal Society of Chemistry, Cambridge, UK, 2014, pp. 697-778.
3. R. F. Heck, Org. React. 1982, 27, 345-390.
4. E. I. Negishi, Angew. Chem. Int. Ed. 2011, 50, 6738-6764;
5. Angew. Chem. 2011, 123, 6870-6897.
6. A. Suzuki, Angew. Chem. Int. Ed. 2011, 50, 6722-6737;
7. Angew. Chem. 2011, 123, 6854-6869.
8. C. C. C. JohanssonSeechurn, M. O. Kitching, T. J. Colacot, V. Snieckus, Angew. Chem. Int. Ed. 2012, 51, 5062-5085;
9. Angew. Chem. 2012, 124, 5150-5174.
10. D. A. Culkin, J. F. Hartwig, Acc. Chem. Res. 2003, 36, 234-245;
11. F. Bellina, R. Rossi, Chem. Rev. 2010, 110, 3850-3850 and
12. F. Bellina, R. Rossi, Chem. Rev. 2010, 110, 1082-1146;
13. C. C. C. Johansson, T. J. Colacot, Angew. Chem. Int. Ed. 2010, 49, 676-707;
14. Angew. Chem. 2010, 122, 686-718;
15. P. Novak, R. Martin, Curr. Org. Chem. 2011, 15, 3233-3262;
16. H. K. Potukuchi, A. P. Spork, T. J. Donohoe, Org. Biomol. Chem. 2015, 13, 4367-4373;
17. S. T. Sivanandan, A. Shaji, I. Ibnusaud, C. C. C. J. Seechurn, T. J. Colacot, Eur. J. Org. Chem. 2015, 38-49.
18. For a noteworthy recent example, see:, T. J. Donohoe, B. S. Pilgrim, G. R. Jones, J. A. Bassuto, Proc. Natl. Acad. Sci. USA 2012, 109, 11605-11608.
19. R. J. Lundgren, M. Stradiotto, Chem. Eur. J. 2012, 18, 9758-9769.
20. For the development of an (NHC)Pd catalyst system that operates at very low catalysts loadings, see:, E. Marelli, M. Corpet, S. R. Davies, S. P. Nolan, Chem. Eur. J. 2014, 20, 17272-17276.
21. G. Danoun, A. Tlili, F. Monnier, M. Taillefer, Angew. Chem. Int. Ed. 2012, 51, 12815-12819;
22. Angew. Chem. 2012, 124, 12987-12991.
23. J. A. Fernández-Salas, E. Marelli, D. B. Cordes, A. M. Slawin, S. P. Nolan, Chem. Eur. J. 2015, 21, 3906-3909.
24. M. Stradiotto, in New Trends in Cross-Coupling: Theory and Application (Ed.:, T.J. Colacot,), Royal Society of Chemistry, Cambridge, UK 2014, pp. 228-253.
25. T. Satoh, Y. Kawamura, M. Miura, M. Nomura, Angew. Chem. Int. Ed. Engl. 1997, 36, 1740-1742;
26. Angew. Chem. 1997, 109, 1820-1822;
27. M. Palucki, S. L. Buchwald, J. Am. Chem. Soc. 1997, 119, 11108-11109;
28. B. C. Hamann, J. F. Hartwig, J. Am. Chem. Soc. 1997, 119, 12382-12383.
29. K. D. Hesp, R. J. Lundgren, M. Stradiotto, J. Am. Chem. Soc. 2011, 133, 5194-5197;
30. P. G. Alsabeh, M. Stradiotto, Angew. Chem. Int. Ed. 2013, 52, 7242-7246;
31. Angew. Chem. 2013, 125, 7383-7387.
32. R. J. Lundgren, B. D. Peters, P. G. Alsabeh, M. Stradiotto, Angew. Chem. Int. Ed. 2010, 49, 4071-4074;
33. Angew. Chem. 2010, 122, 4165-4168.
34. P. B. Li, B. Lu, C. L. Fu, S. M. Ma, Adv. Synth. Catal. 2013, 355, 1255-1259;
35. C. Gäbler, M. Korb, D. Schaarschmidt, A. Hildebrandt, H. Lang, Adv. Synth. Catal. 2014, 356, 2979-2983.
36. L. Ackermann, V. P. Mehta, Chem. Eur. J. 2012, 18, 10230-10233.
37. N. L. Rotta-Loria, A. Borzenko, P. G. Alsabeh, C. B. Lavery, M. Stradiotto, Adv. Synth. Catal. 2015, 357, 100-106.
38. J. Schranck, A. Tlili, P. G. Alsabeh, H. Neumann, M. Stradiotto, M. Beller, Chem. Eur. J. 2013, 19, 12624-12628.
39. A. F. Littke, G. C. Fu, J. Am. Chem. Soc. 2001, 123, 6989-7000;
40. G. Adjabeng, T. Brenstrum, J. Wilson, C. Frampton, A. Robertson, J. Hillhouse, J. McNulty, A. Capretta, Org. Lett. 2003, 5, 953-955;
41. T. E. Barder, S. D. Walker, J. R. Martinelli, S. L. Buchwald, J. Am. Chem. Soc. 2005, 127, 4685-4696;
42. N. Marion, O. Navarro, J. G. Mei, E. D. Stevens, N. M. Scott, S. P. Nolan, J. Am. Chem. Soc. 2006, 128, 4101-4111;
43. O. Navarro, N. Marion, J. G. Mei, S. P. Nolan, Chem. Eur. J. 2006, 12, 5142-5148;
44. E. Alvaro, J. F. Hartwig, J. Am. Chem. Soc. 2009, 131, 7858-7868;
45. C. Han, S. L. Buchwald, J. Am. Chem. Soc. 2009, 131, 7532-7533;
46. A. G. Sergeev, T. Schulz, C. Torborg, A. Spannenberg, H. Neumann, M. Beller, Angew. Chem. Int. Ed. 2009, 48, 7595-7599;
47. Angew. Chem. 2009, 121, 7731-7735;
48. M. Pompeo, R. D. Froese, N. Hadei, M. G. Organ, Angew. Chem. Int. Ed. 2012, 51, 11354-11357;
49. Angew. Chem. 2012, 124, 11516-11519;
50. P. G. Alsabeh, R. J. Lundgren, R. McDonald, C. C. JohanssonSeechurn, T. J. Colacot, M. Stradiotto, Chem. Eur. J. 2013, 19, 2131-2141;
51. G.-p. Lu, C. Cai, B. H. Lipshutz, Green Chem. 2013, 15, 105;
52. C. A. Wheaton, J.-P. J. Bow, M. Stradiotto, Organometallics 2013, 32, 6148-6161;
53. J. L. Farmer, M. Pompeo, A. J. Lough, M. G. Organ, Chem. Eur. J. 2014, 20, 15790-15798;
54. M. Pompeo, J. L. Farmer, R. D. Froese, M. G. Organ, Angew. Chem. Int. Ed. 2014, 53, 3223-3226;
55. Angew. Chem. 2014, 126, 3287-3290;
56. J. Zhang, A. Bellomo, N. Trongsiriwat, T. Jia, P. J. Carroll, S. D. Dreher, M. T. Tudge, H. Yin, J. R. Robinson, E. J. Schelter, P. J. Walsh, J. Am. Chem. Soc. 2014, 136, 6276-6287.
57. R. Singh, S. P. Nolan, J. Organomet. Chem. 2005, 690, 5832-5840.
58. H. U. Blaser, W. Brieden, B. Pugin, F. Spindler, M. Studer, A. Togni, Top. Catal. 2002, 19, 3-16.
59. B. P. Fors, D. A. Watson, M. R. Biscoe, S. L. Buchwald, J. Am. Chem. Soc. 2008, 130, 13552-13554.
60. Q. L. Shen, J. F. Hartwig, J. Am. Chem. Soc. 2006, 128, 10028-10029;
61. G. D. Vo, J. F. Hartwig, J. Am. Chem. Soc. 2009, 131, 11049-11061.