Palladium-catalyzed cross-coupling of α-bromocarbonyls and allylic alcohols for the synthesis of α-aryl dicarbonyl compounds

Chemical Science

Volumn 6, Issue 5, 2015, Pages 2777-2781

  Yu, Yang ^a   Tambar, Uttam K ^a  

^a UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; FREE RADICALS; OLEFINS; PALLADIUM COMPOUNDS;

ACYL RADICALS; ALLYLIC ALCOHOL; DICARBONYL COMPOUNDS; ORGANOHALIDES; PALLADIUM-CATALYZED; PALLADIUM-CATALYZED CROSS-COUPLINGS; SYNTHESIZING COMPLEX;

SYNTHESIS (CHEMICAL);

EID: 84928158871     PISSN: 20416520     EISSN: 20416539     Source Type: Journal    
DOI: 10.1039/c5sc00505a     Document Type: Article

References (74)

1. R. F. Heck J. Am. Chem. Soc. 1968 90 5518 5526
2. T. Mizoroki K. Mori A. Ozaki Bull. Chem. Soc. Jpn. 1971 44 581 581
3. R. F. Heck J. P. Nolley J. Org. Chem. 1972 37 2320 2322
4. A. de Meijere F. E. Meyer Angew. Chem., Int. Ed. 1995 33 2379 2411
5. I. P. Beletskaya A. V. Cheprakov Chem. Rev. 2000 100 3009 3066
6. A. B. Dounay L. E. Overman Chem. Rev. 2003 103 2945 2964
7. R. F. Heck Org. React. 1982 27 345 390
8. M. Oestreich and Editor, The Mizoroki-Heck Reaction, John Wiley & Sons Ltd., 2009
9. C. Torborg M. Beller Adv. Synth. Catal. 2009 351 3027 3043
10. C. C. C. Johansson Seechurn M. O. Kitching T. J. Colacot V. Snieckus Angew. Chem., Int. Ed. 2012 51 5062 5085
11. Y. Ikeda T. Nakamura H. Yorimitsu K. Oshima J. Am. Chem. Soc. 2002 124 6514 6515
12. W. Affo H. Ohmiya T. Fujioka Y. Ikeda T. Nakamura H. Yorimitsu K. Oshima Y. Imamura T. Mizuta K. Miyoshi J. Am. Chem. Soc. 2006 128 8068 8077
13. L. Firmansjah G. C. Fu J. Am. Chem. Soc. 2007 129 11340 11341
14. K. S. Bloome E. J. Alexanian J. Am. Chem. Soc. 2010 132 12823 12825
15. K. S. Bloome R. L. McMahen E. J. Alexanian J. Am. Chem. Soc. 2011 133 20146 20148
16. M. E. Weiss L. M. Kreis A. Lauber E. M. Carreira Angew. Chem., Int. Ed. 2011 50 11125 11128
17. E. W. Werner M. S. Sigman J. Am. Chem. Soc. 2011 133 9692 9695
18. E. W. Werner T.-S. Mei A. J. Burckle M. S. Sigman Science 2012 338 1455 1458
19. Z. Yang J. Zhou J. Am. Chem. Soc. 2012 134 11833 11835
20. T. W. Liwosz S. R. Chemler Org. Lett. 2013 15 3034 3037
21. T.-S. Mei E. W. Werner A. J. Burckle M. S. Sigman J. Am. Chem. Soc. 2013 135 6830 6833
22. E. A. Standley T. F. Jamison J. Am. Chem. Soc. 2013 135 1585 1592
23. M. R. Harris M. O. Konev E. R. Jarvo J. Am. Chem. Soc. 2014 136 7825 7828
24. T.-S. Mei H. H. Patel M. S. Sigman Nature 2014 508 340 344
25. M. Oestreich Angew. Chem., Int. Ed. 2014 53 2282 2285
26. L. Xu M. J. Hilton X. Zhang P.-O. Norrby Y.-D. Wu M. S. Sigman O. Wiest J. Am. Chem. Soc. 2014 136 1960 1967
27. A. J. Chalk S. A. Magennis J. Org. Chem. 1976 41 273 278
28. A. J. Chalk S. A. Magennis J. Org. Chem. 1976 41 1206 1209
29. J. B. Melpolder R. F. Heck J. Org. Chem. 1976 41 265 272
30. Y. Tamaru Y. Yamada Z.-i. Yoshida Tetrahedron Lett. 1977 18 3365 3368
31. Y. Tamaru Y. Yamada Z.-i. Yoshida Tetrahedron Lett. 1978 19 919 922
32. J.-M. Gaudin Tetrahedron Lett. 1991 32 6113 6116
33. D. Basavaiah K. Muthukumaran Tetrahedron 1998 54 4943 4948
34. B. M. Trost J. R. Corte M. S. Gudiksen Angew. Chem., Int. Ed. 1999 38 3662 3664
35. M.-S. Schiedel C. A. Briehn P. Bäuerle Angew. Chem., Int. Ed. 2001 40 4677 4680
36. F. Berthiol H. Doucet M. Santelli Tetrahedron Lett. 2004 45 5633 5636
37. F. Berthiol H. Doucet M. Santelli Appl. Organomet. Chem. 2006 20 855 868
38. F. Berthiol H. Doucet M. Santelli Tetrahedron 2006 62 4372 4383
39. V. Calò A. Nacci A. Monopoli V. Ferola J. Org. Chem. 2007 72 2596 2601
40. G. Satyanarayana M. E. Maier Org. Lett. 2008 10 2361 2364
41. E. A. Voight H. Yin S. V. Downing S. A. Calad H. Matsuhashi I. Giordano A. J. Hennessy R. M. Goodman J. L. Wood Org. Lett. 2010 12 3422 3425
42. A. Sauza J. A. Morales-Serna M. García-Molina R. Gaviño J. Cárdenas Synthesis 2012 272 282
43. Q. Liu H. Yi J. Liu Y. Yang X. Zhang Z. Zeng A. Lei Chem.-Eur. J. 2013 19 5120 5126
44. T. Nishikata Y. Noda R. Fujimoto T. Sakashita J. Am. Chem. Soc. 2013 135 16372 16375
45. J. Christoffers J. Chem. Soc., Perkin Trans. 1 1997 3141 3150
46. M. J. Chapdelaine M. Hulce Org. React. 2004 38 225 653
47. F. Guo M. D. Clift R. J. Thomson Eur. J. Org. Chem. 2012 4881 4896
48. A.-M. R. Dechert-Schmitt D. C. Schmitt X. Gao T. Itoh M. J. Krische Nat. Prod. Rep. 2014 31 504 513
49. Y. Zhao A. Aguilar D. Bernard S. Wang J. Med. Chem. 2015 58 1038 1052
50. X. Liu F. Xiong X. Huang L. Xu P. Li X. Wu Angew. Chem., Int. Ed. 2013 52 6962 6966
51. X.-Q. Chu H. Meng Y. Zi X.-P. Xu S.-J. Ji Chem. Commun. 2014 50 9718 9721
52. X.-Q. Chu Y. Zi H. Meng X.-P. Xu S.-J. Ji Chem. Commun. 2014 50 7642 7645
53. A. Bunescu Q. Wang J. Zhu Angew. Chem., Int. Ed. 2015 54 3132 3135
54. See ESI† for more complete optimization tables
55. M. Naodovic H. Yamamoto Chem. Rev. 2008 108 3132 3148
56. J.-M. Weibel A. Blanc P. Pale Chem. Rev. 2008 108 3149 3173
57. J.-H. Fan W.-T. Wei M.-B. Zhou R.-J. Song J.-H. Li Angew. Chem., Int. Ed. 2014 53 6650 6654
58. S. J. Blanksby G. B. Ellison Acc. Chem. Res. 2003 36 255 263
59. The observation of small amounts of cyclopropyl-migration and no methyl-migration (entries 11 vs. 10) may be rationalized by a ring-expanded cyclobutyl intermediate during the 1,2-migration step in Table 2, entry 11.
60. B. S. Lucas B. Fisher L. R. McGee S. H. Olson J. C. Medina E. Cheung J. Am. Chem. Soc. 2012 134 12855 12860
61. S. Nahm S. M. Weinreb Tetrahedron Lett. 1981 22 3815 3818
62. A. Studer M. Bossart Tetrahedron 2001 57 9649 9667
63. See ESI† for detailed X-ray crystallographic data.
64. M. Newcomb Tetrahedron 1993 49 1151 1176
65. D. A. Lindsay J. Lusztyk K. U. Ingold J. Am. Chem. Soc. 1984 106 7087 7093
66. Although it is possible that the TEMPO adduct of free radical 15 is not observed because acyl-radical 13 is completely consumed by TEMPO before 15 is generated, our observation of trace amounts of product 17 even in the presence of TEMPO is not consistent with this alternate explanation.
67. W. H. Urry M. S. Kharasch J. Am. Chem. Soc. 1944 66 1438 1440
68. A. Effio D. Griller K. U. Ingold J. C. Scaiano S. J. Sheng J. Am. Chem. Soc. 1980 102 6063 6068
69. A. N. Abeywickrema A. L. J. Beckwith S. Gerba J. Org. Chem. 1987 52 4072 4078
70. R. Leardini D. Nanni G. F. Pedulli A. Tundo G. Zanardi E. Foresti P. Palmieri J. Am. Chem. Soc. 1989 111 7723 7732
71. B. Giese Angew. Chem., Int. Ed. 1989 28 969 980
72. N. A. Porter B. Giese D. P. Curran Acc. Chem. Res. 1991 24 296 304
73. A. Gansäuer H. Bluhm Chem. Rev. 2000 100 2771 2788
74. M. P. Sibi S. Manyem J. Zimmerman Chem. Rev. 2003 103 3263 3296