Copper-catalyzed cross-coupling of O -alkyl hydroxamates with aryl iodides

Synthesis (Germany)

Volumn 44, Issue 15, 2012, Pages 2413-2423

  Kukosha, Tatyana ^a   Trufilkina, Nadezhda ^a   Belyakov, Sergey ^a   Katkevics, Martins ^a  

^a LATVIAN INSTITUTE OF ORGANIC SYNTHESIS   (Latvia)

Author keywords

amides; arylation; catalysis; copper; cross coupling; halides

Indexed keywords

ACID DERIVATIVE; ARYL IODIDES; ARYLATIONS; CROSS-COUPLINGS; HALIDES; REACTION CONDITIONS;

AMIDES; CATALYSIS; REACTION KINETICS;

COPPER;

3 (2 BROMOPHENYL) N METHOXY N PHENYLPROPANAMIDE; 3 (2 CHLOROPHENYL) N METHOXY N PHENYLACETAMIDE; 3 (2 IODOPHENYL) N METHOXY N PHENYLPROPANAMIDE; ARYL IODIDE DERIVATIVE; HYDROXAMIC ACID DERIVATIVE; IODINE DERIVATIVE; N (4 ACETYLPHENYL) N (ALLYLOXY) 2 PHENYLACETAMIDE; N (4 ACETYLPHENYL) N METHOXY 2 PHENYLACETAMIDE; N (ALLYLOXY) N (4 NITROPHENYL) 2 PHENYLACETAMIDE; N (ALLYLOXY) N PHENYLBENZAMIDE; N (ALLYLOXY) N,2 DIPHENYLACETAMIDE; N (BENZYLOXY) N,2 DIPHENYLACETAMIDE; N (TERT BUTOXY) N,2 DIPHENYLACETAMIDE; N METHOXY N (3 NITROPHENYL) 2 PHENYLACETAMIDE; N METHOXY N (4 NITROPHENYL) 2 PHENYLACETAMIDE; N METHOXY N PHENYL 4 (TRIFLUOROMETHYL)BENZAMIDE; N METHOXY N PHENYLBENZAMIDE; N METHOXY N PHENYLCYCLOHEXANECARBOXAMIDE; N METHOXY N PHENYLFURAN 2 CARBOXAMIDE; N METHOXY N PHENYLFURAN 3 CARBOXAMIDE; N METHOXY N PHENYLPENTANAMIDE; N METHOXY N PHENYLTETRAHYDROFURAN 2 CARBOXAMIDE; N METHOXY N PHENYLTHIOPHENE 3 CARBOXAMIDE; N METHOXY N,1 DIPHENYLCYCLOPROPANECARBOXAMIDE; N METHOXY N,2 DIPHENYLACETAMIDE; N METHOXY N,2 DIPHENYLPROPANAMIDE; N,2 DIPHENYL N (TETRAHYDRO 2H PYRAN 2 YLOXY)ACETAMIDE; N,4 DIMETHOXY N PHENYLBENZAMIDE; O ALKYL HYDROXAMATE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CRYSTALLOGRAPHY; CYCLIZATION; DIELS ALDER REACTION; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION TIME; SYNTHESIS;

EID: 84864286155     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0031-1290384     Document Type: Article

References (84)

1. Mohri K, Oikawa Y, Hirao K.-i, Yonemitsu O. Heterocycles: 1982; 19 515
2. Mohri K, Oikawa Y, Hirao K.-i, Yonemitsu O. Chem. Pharm. Bull.: 1982; 30 3097
3. Blechert S. Tetrahedron Lett.: 1984; 25 1547
4. Martin P. Tetrahedron Lett.: 1987; 28 1645
5. Martin P. Helv. Chim. Acta: 1984; 67 1647
6. Martin P. Helv. Chim. Acta: 1988; 71 344
7. Martin P. Helv. Chim. Acta: 1989; 72 1554
8. Tomioka Y, Ohkubo K, Maruoka H. J. Heterocycl. Chem.: 2007; 44 419
9. Kalkote UR, Goswami DD. Aust. J. Chem.: 1977; 30 1847
10. Sheradsky T, Avramovici-Grisaru S. J. Heterocycl. Chem.: 1980; 17 189
11. Shi G.-q. Tetrahedron Lett.: 2000; 41 2295
12. Mohri K, Oikawa Y, Hirao K.-i, Yonemitsu O. Heterocycles: 1982; 19 521
13. Sugai S, Sato K, Ueda T, Kataoka K, Tomita K. Heterocycles: 1983; 20 1123
14. Tabei K, Kawashima E, Kato T. Chem. Pharm. Bull.: 1979; 27 1842
15. Procter G, Nally J, Ordsmith NH. R. Tetrahedron: 1995; 51 12837
16. Schmidt VA, Alexanian EJ. Angew. Chem. Int. Ed.: 2010; 49 4491
17. Schmidt VA, Alexanian EJ. J. Am. Chem. Soc.: 2011; 133 11402
18. Almeida PS, Lobo AM, Prabhakar S. Heterocycles: 1989; 28 653
19. Wassmundt FW, Babic GT. J. Org. Chem.: 1982; 47 3585
20. Fauq AH, Simpson K, Maharvi GM, Golde T, Das P. Bioorg. Med. Chem. Lett.: 2007; 17 6392
21. Geffken D, Geisel S. J. Heterocycl. Chem.: 1994; 31 1473
22. De Amici M, Magri P, De Micheli C, Cateni F, Bovara R, Carrea G, Riva S, Casalone G. J. Org. Chem.: 1992; 57 2825
23. Nakamura I, Sato Y, Terada M. J. Am. Chem. Soc.: 2009; 131 4198
24. Aires-de-Sousa J, Lobo AM, Prabhakar S. Tetrahedron Lett.: 1996; 37 3183
25. Aires-de-Sousa J, Prabhakar S, Lobo AM, Rosa AM, Gomes MJ. S, Corvo MC, Williams DJ, White AJ. P. Tetrahedron: Asymmetry: 2001; 12 3349
26. Murugan E, Siva A. Synthesis: 2005; 2022
27. Corminboeuf O, Renaud P. Org. Lett.: 2002; 4 1731
28. Corminboeuf O, Renaud P. Org. Lett.: 2002; 4 1735
29. Kulys J, Deussen H.-J, Krikstopaitis K, Lolck R, Schneider P, Ziemys A. Eur. J. Org. Chem.: 2001; 3475
30. Xu F, Deussen H.-JW, Lopez B, Lam L, Li K. Eur. J. Biochem.: 2001; 268 4169
31. Si TK, Chowdhury K, Mukherjee M, Bera DC, Bhattacharyya R. J. Mol. Catal. A: Chem.: 2004; 219 241
32. Maiti SK, Malik KM. A, Gupta S, Chakraborty S, Ganguli AK, Mukherjee AK, Bhattacharyya R. Inorg. Chem.: 2006; 45 9843
33. Maiti SK, Dinda S, Banerjee S, Mukherjee AK, Bhattacharyya R. Eur. J. Inorg. Chem.: 2008; 2038
34. Mangold BL. K, Hanna PE. J. Med. Chem.: 1982; 25 630
35. Yeh H.-m, Hanna PE. J. Med. Chem.: 1982; 25 842
36. Marhevka VC, Ebner NA, Sehon RD, Hanna PE. J. Med. Chem.: 1985; 28 18
37. Musser JH, Kubrak DM, Chang J, Lewis AJ. J. Med. Chem.: 1986; 29 1429
38. Musser JH, Kubrak DM, Chang J, DiZio SM, Hite M, Hand JM, Lewis AJ. J. Med. Chem.: 1987; 30 400
39. Gassman PG, Granrud JE. J. Am. Chem. Soc.: 1984; 106 1498
40. Lobo MA, Marques MM, Prabhakar S, Rzepa HS. J. Org. Chem.: 1987; 52 2925
41. Corbett MD, Corbett BR, Doerge DR. J. Chem. Soc., Perkin Trans. 1: 1982; 345; and references cited therein
42. Corbett MD, Doerge DR, Corbett BR. J. Chem. Soc., Perkin Trans. 1: 1983; 765
43. Sakamoto Y, Yoshioka T, Uematsu T. J. Org. Chem.: 1989; 54 4449
44. Pilepić V, Lovrek M, Vikić-Topić D, Uršić S. Tetrahedron Lett.: 2001; 42 8519
45. Vrček IV, Pilepić V, Uršić S. Tetrahedron Lett.: 2004; 45 699
46. Ferreira LM, Marques MM. B, Glória PM. C, Chaves HT, Franco J.-PP, Mourato I, Antunes J.-RT, Rzepa HS, Lobo AM, Prabhakar S. Tetrahedron: 2008; 64 7759
47. Wong FT, Patra PK, Seayad J, Zhang Y, Ying JY. Org. Lett.: 2008; 10 2333
48. Ayhan P, Demir AS. Adv. Synth. Catal.: 2011; 353 624
49. Wasa M, Yu J.-Q. J. Am. Chem. Soc.: 2008; 130 14058
50. Wang G.-W, Yuan T.-T, Li D.-D. Angew. Chem. Int. Ed.: 2011; 50 1380
51. Evano G, Blanchard N, Toumi M. Chem. Rev.: 2008; 108 3054
52. Wang C, Liu L, Wang W, Ma D.-S, Zhang H. Molecules: 2010; 15 1154
53. Ali A, Saha P, Punniyamurthy T. Synthesis: 2010; 908
54. Hicks JD, Hyde AM, Cuezva AM, Buchwald SL. J. Am. Chem. Soc.: 2009; 131 16720; and references cited therein
55. Rosen BR, Ruble JC, Beauchamp TJ, Navarro A. Org. Lett.: 2011; 13 2564; and references cited therein
56. Shekhar S, Dunn TB, Kotecki BJ, Montavon DK, Cullen SC. J. Org. Chem.: 2011; 76 4552
57. Teo Y.-C, Yong F.-F. Synlett: 2011; 837
58. Wang X, Guram A, Ronk M, Milne JE, Tedrow JS, Faul MM. Tetrahedron Lett.: 2012; 53 7
59. Miyasaka M, Hirano K, Satoh T, Kowalczyk R, Bolm C, Miura M. Org. Lett.: 2011; 13 359; and references cited therein
60. Yongpruksa N, Calkins NL, Harmata M. Chem. Commun. (Cambridge): 2011; 47 7665
61. Azzaro S, Desage-El Murr M, Fensterbank L, Lacôte E, Malacria M. Synlett: 2011; 849
62. Worch C, Bolm C. Synthesis: 2008; 739
63. Tanimori S, Ozaki Y, Iesaki Y, Kirihata M. Synlett: 2008; 1973
64. Liu R, Zhu Y.-m, Qin L.-n, Katayama H. Heterocycles: 2007; 71 1755
65. Wolter M, Klapars A, Buchwald SL. Org. Lett.: 2001; 3 3803
66. Xie X, Ni G, Ma F, Ding L, Xu S, Zhang Z. Synlett: 2011; 955
67. Lefebvre V, Cailly T, Fabis F, Rault S. J. Org. Chem.: 2010; 75 2730
68. Inamoto K, Katsuno M, Yoshino T, Arai Y, Hiroya K, Sakamoto T. Tetrahedron: 2007; 63 2695
69. Ma F.-F, Peng Z.-Y, Li W.-F, Xie X.-M, Zhang Z. Synlett: 2011; 2555; and references cited therein
70. Halland N, Nazaré M, R'kyek O, Alonso J, Urmann M, Lindeschmidt A. Angew. Chem. Int. Ed.: 2009; 48 6879
71. Jiang L, Lu X, Zhang H, Jiang Y, Ma D. J. Org. Chem.: 2009; 74 4542
72. Jones KL, Porzelle A, Hall A, Woodrow MD, Tomkinson NC. O. Org. Lett.: 2008; 10 797
73. Porzelle A, Woodrow MD, Tomkinson NC. O. Org. Lett.: 2009; 11 233
74. Nielsen SD, Smith G, Begtrup M, Kristensen JL. Eur. J. Org. Chem.: 2010; 3704
75. Beaudoin D, Wuest JD. Tetrahedron Lett.: 2011; 52 2221
76. Grimm JB, Lavis LD. Org. Lett.: 2011; 13 6354
77. Klapars A, Huang X, Buchwald SL. J. Am. Chem. Soc.: 2002; 124 7421
78. Strieter ER, Blackmond DG, Buchwald SL. J. Am. Chem. Soc.: 2005; 127 4120
79. Tye JW, Weng Z, Johns AM, Incarviro CD, Hartwig JF. J. Am. Chem. Soc.: 2008; 130 9971
80. Strieter ER, Bhayana B, Buchwald SL. J. Am. Chem. Soc.: 2009; 131 78
81. Jones GO, Liu P, Houk KN, Buchwald SL. J. Am. Chem. Soc.: 2010; 132 6205
82. Vakulka AA, Filinchuk YaE, Mys'kiv MG. Russ. J. Coord. Chem. (Engl. Transl.): 2007; 33 809
83. Fukushima K, Kobayashi A, Miyamoto T, Sasaki Y. Bull. Chem. Soc. Jpn.: 1976; 143
84. Nelson SM, Lavery A, Drew MG. B. J. Chem. Soc., Dalton Trans.: 1986; 911