Alkene synthesis through transition metal-catalyzed cross-coupling of N-tosylhydrazones

Topics in Current Chemistry

Volumn 327, Issue , 2012, Pages 239-270

  Zhang, Yan ^a   Wang, Jianbo ^a  

^a PEKING UNIVERSITY   (China)

Author keywords

Alkene synthesis; Cross coupling; Metal carbene; N Tosylhydrazones

Indexed keywords

ALKENE; HYDRAZONE DERIVATIVE; TRANSITION ELEMENT;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ALKENES; CATALYSIS; HYDRAZONES; MOLECULAR STRUCTURE; TRANSITION ELEMENTS;

EID: 84867007165     PISSN: 03401022     EISSN: None     Source Type: Book Series    
DOI: 10.1007/128-2012-322     Document Type: Article

References (109)

1. Bamford WR, Stevens TS (1952) J Chem Soc 4735-4740
2. Shapiro RH (1976) Org React 23:405-507
3. Vedejs E, Dolphin JM, Stolle WT (1979) J Am Chem Soc 101:249-251
4. Li P, Zhao J, Wu C, Larock RC, Shi F (2011) Org Lett 13:3340-3343
5. Inamoto K (2008) Yakugaku Zasshi 128:997-1005
6. Friedman L, Shechter H (1961) J Am Chem Soc 83:3159-3160
7. Kirmse W, Buschoff M (1967) Chem Ber 100:1491-1506
8. Shapiro RH, Duncan JH, Clopton JC (1967) J Am Chem Soc 89:471-472
9. Kenar JA, Nickon A (1997) Tetrahedron 53:14871-14894
10. Olmstead KK, Nickon A (1999) Tetrahedron 55:3585-3594
11. Shapiro RH, Heath MJ (1967) J Am Chem Soc 89:5734-5735
12. Adlington RM, Barrett AGM (1983) Acc Chem Res 16:55-59
13. Nicolaou KC, Yang Z, Liu JJ, Ueno H, Nantermet PG, Guy RK, Claiborne CF, Renaud J, Couladouros EA, Paulvannan K, Sorensen EJ (1994) Nature 367:630-634
14. Mayr M, Bataille CJR, Gosiewska S, Raskatov JA, Brown JM (2008) Tetrahedron Asymmetry 19:1328-1332
15. Reduction of carbonyl compounds to alkenes. In: Sundberg RJ, Carey FA (eds) Advanced organic chemistry part B, 5th edn. Springer Science, Business Media, LLC
16. Vedejs E, Stolle WT (1977) Tetrahedron Lett 18:135-138
17. Chamberlin R, Bloom SH (1990) Org React 39:1-83
18. Taylor EJ, Djerassi C (1976) J Am Chem Soc 98:2275-2281
19. Hutchins RO, Kacher M, Rua L (1975) J Org Chem 40:923-926
20. Girotra NN, Wendler NL (1982) Tetrahedron Lett 23:5501-5504
21. Greco MN, Maryanoff BE (1992) Tetrahedron Lett 33:5009-5012
22. Staudinger H, Siegwart J (1920) Helv Chim Acta 3:833-840
23. Barton DHR, Smith EH, Willis BJ (1970) J Chem Soc D 1225-1226
24. Kellogg RM, Wassenaar S (1970) Tetrahedron Lett 11:1987-1990
25. Garratt PJ, Payne D, Tocher DA (1990) J Org Chem 55:1909-1915
26. Wagner K, Weiss D, Beckert R (2000) Eur J Org Chem 3001-3005
27. Shimasaki T, Kato S-i, Shinmyozu T (2007) J Org Chem 72:6251-6254
28. Seyfrieda MS, Lindena A, Mlostoń G, Heimgartner H (2009) Helv Chim Acta 92:1800-1816
29. Plunkett KN, Godula K, Nuckolls C, Tremblay N, Whalley AC, Xiao S (2009) Org Lett 11:2225-2228
30. Pijper TC, Pijper D, Pollard MM, Dumur F, Davey SG, Meetsma A, Feringa BL (2010) J Org Chem 75:825-838
31. Ciscato LFML, Bastos EL, Bartoloni FH, Gunther W, Weiss D, Beckert R, Baader WJ (2010) J Braz Chem Soc 21:1896-1904
32. Katritzky AR, Tymoshenko DO, Belyakov SA (1999) J Org Chem 64:3332-3334
33. Katritzky AR, Wang J, Karodia N, Li J (1997) J Org Chem 62:4142-4147
34. Kurek-Tyrlik A, Marczak S, Michalak K, Wicha J, Zarecki A (2001) J Org Chem 66:6994-7001
35. Chandrasekhar S, Takhi M, Yadav JS (1995) Tetrahedron Lett 36:307-310
36. Chandrasekhar S, Takhi M, Yadav JS (1995) Tetrahedron Lett 36:5071-5074
37. Chandrasekhar S, Reddy MV, Rajaiah G (2000) Tetrahedron Lett 41:10131-10134
38. Yadav JS, Chandrasekhar S, Sasmal PK (1997) Tetrahedron Lett 38:8765-8768
39. Chandrasekhar S, Reddy MV, Takhi M (1999) Tetrahedron Lett 39:6535-6538
40. Wicha J, Zarecki A (2004) J Org Chem 69:5810-5812
41. Jung ME, Hagiwara A (1991) Tetrahedron Lett 32:3025-3028
42. Frimer AA, Weiss J, Rosental Z (1994) J Org Chem 59:2516-2522
43. Kabalka GW, Wu Z, Ju YH (2001) Tetrahedron Lett 42:4759-4760
44. Feng X-W, Wang J, Zhang J, Yang J, Wang N, Yu X-Q (2010) Org Lett 12:4408-4410
45. Doyle MP, Forbes DC (1998) Chem Rev 98:911-935
46. Doyle MP, Duffy R, Ratnikov M, Zhou L (2010) Chem Rev 110:704-724
47. Maas G (2004) Chem Soc Rev 33:183-190
48. Zhang Z, Wang JB (2008) Tetrahedron 64:6577-6605
49. Aggarwal VK, de Vicente J, Bonnert RV (2001) Org Lett 3:2785-2788
50. Aggarwal VK, Alonso E, Hynd G, Lydon KM, Palmer MJ, Porcelloni M, Studley JR (2001) Angew Chem Int Ed 41:1430-1433
51. Aggarwal VK, Patel M, Studley J (2002) Chem Commun 38:1514-1515
52. Aggarwal VK, Alonso E, Bae I, Hynd G, Lydon KM, Palmer MJ, Patel M, Porcelloni M, Richardson J, Stenson RA, Studley JR, Vasse J-L, Winn CL (2003) J Am Chem Soc 125:10926-10940
53. Doyle MP, Yan M (2002) J Org Chem 67:602-604
54. Doyle MP, Hu W, Phillips IM (2002) Org Lett 2:1777-1779
55. Xiao F, Wang J (2006) J Org Chem 71:5789-5791
56. Bronstein HE, Choi N, Scott LT (2002) J Am Chem Soc 124:8870-8875
57. Smegal JA, Meier IK, Schwartz J (1986) J Am Chem Soc 108:1322-1323
58. Lu X, Fang H, Ni Z (1989) J Organomet Chem 373:77-84
59. Lee M-Y, Chen Y, Zhang XP (2003) Organometallics 22:4905-4909
60. Kuhn FE, Santos AM (2004) Mini-Rev Org Chem 1:55-64
61. Herrmann WA, Wang M (1991) Angew Chem Int Ed 30:1641-1643
62. Fujimura O, Honma T (1998) Tetrahedron Lett 39:625-626
63. Mirafzal GA, Cheng G, Woo LK (2002) J Am Chem Soc 124:176-177
64. Cheng G, Mirafzal GA, Woo LK (2003) Organometallics 22:1468-1474
65. Lebel H, Davi M (2008) Adv Synth Catal 350:2352-2358
66. Aggarwal VK, Fulton JR, Sheldon CG, de Vicente J (2003) J Am Chem Soc 125:6034-6035
67. Fulton JR, Aggarwal VK, de Vicente J (2005) Eur J Org Chem 1479-1492
68. Zhu S, Liao Y, Zhu S (2004) Org Lett 6:377-380
69. Reiser O (2006) Angew Chem Int Ed 45:2838-2840
70. Torborg C, Beller M (2009) Adv Synth Catal 351:3027-3043
71. Wu X-F, Anbarasan P, Neumann H, Beller M (2010) Angew Chem Int Ed 49:9047-9050
72. Zhang Y, Wang J (2011) Eur J Org Chem 1015-1026
73. Greenman KL, Carter DS, Van Vranken DL (2001) Tetrahedron 57:5219-5225
74. Franssen NMG, Walters AJC, Reek JNH, de Bruin B (2011) Catal Sci Technol 1:153-165
75. Barluenga J, Valdés C (2011) Angew Chem Int Ed 50:7486-7500
76. Shao Z, Zhang H (2011) Chem Soc Rev 41:560-572
77. Greenman KL, Van Vranken DL (2005) Tetrahedron 61:6438-6441
78. Devine SK, Van Vranken DL (2007) Org Lett 9:2047-2049
79. Kudirka R, Devine SKJ, Adams CS, Van Vranken DL (2009) Angew Chem Int Ed 48:3677-3680
80. Devine SKJ, Van Vranken DL (2008) Org Lett 10:1909-1911
81. Kudirka R, Van Vranken DL (2008) J Org Chem 73:3585-3588
82. Yu W-Y, Tsoi Y, Zhou Z, Chan ASC (2009) Org Lett 11:469-472
83. Tsoi Y-T, Zhou Z, Chan ASC, Yu W-Y (2010) Org Lett 12:4506-4509
84. Peng C, Wang Y, Wang J (2008) J Am Chem Soc 130:1566-1567
85. Chen S, Wang J (2008) Chem Commun 44:4198-4200
86. Peng C, Yan G, Wang Y, Jiang Y, Zhang Y, Wang J (2010) Synthesis 24:4154-4168
87. Barluenga J, Moriel P, Valdés C, Aznar F (2007) Angew Chem Int Ed 46:5587-5590
88. Messaoudi S, Tréguier B, Hamze A, Morvan E, Brion J-D, Alami M (2009) J Med Chem 52:4538-4542
89. Barluenga J, Tomás-Gamasa M, Moriel P (2008) Chem Eur J 14:4792-4795
90. Brachet E, Hamze A, Peyrat J-F, Brion J-D, Alami M (2010) Org Lett 12:4042-4045
91. Barluenga J, Tomás-Gamasa M, Aznar F, Valdés C (2010) Chem Eur J 16:12801-12803
92. Barluenga J, Escribano M, Moriel P, Aznar F, Valdés C (2009) Chem Eur J 15:13291-13294
93. Rasolofonjatovo E, Tréguier B, Provot O, Hamze A, Morvan E, Brion J-D, Alami M (2011) Tetrahedron Lett 52:1036-1040
94. Barluenga J, Florentino L, Aznar F, Valdés C (2011) Org Lett 13:510-513
95. Davies HML, Huby NJS, Cantrell WR Jr, Olive JL (1993) J Am Chem Soc 115:9468-9479
96. Corradi A, Leonelli C, Rizzuti A, Rosa R, Veronesi P, Grandi R, Baldassari S, Villa C (2007) Molecules 12:1482-1495
97. Fustero S, Simón-Fuentes A, Sanz-Cervera JF (2009) Org Prep Proced Int 41:253-290
98. Barluenga J, Tomás-Gamasa M, Aznar F (2010) Adv Synth Catal 352:3235-3240
99. Barluenga J, Escribano M, Aznar F, Valdés C (2010) Angew Chem Int Ed 49:6856-6859
100. Hartwig JF (2004) Palladium-catalyzed amination of aryl halides and sulfonates. In: Astruc D (ed) Modern arene chemistry. Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, FRG
101. Liao X, Weng Z, Hartwig JF (2008) J Am Chem Soc 130:195-200
102. Tréguier B, Hamze A, Provot O, Brion J-D, Alami M (2009) Tetrahedron Lett 50:6549-6552
103. Zhao X, Jing J, Lu K, Zhang Y, Wang J (2010) Chem Commun 46:1724-1726
104. Zhou L, Ye F, Ma J, Wang J (2011) Angew Chem Int Ed 50:3510-3514
105. Chen Z-S, Duan X-H, Wu L-Y, Ali S, Ji K-G, Zhou P-X, Liu X-Y, Liang Y-M (2011) Chem Eur J 17:6918-6921
106. Xiao Q, Ma J, Yang Y, Zhang Y, Wang J (2009) Org Lett 11:4732-4735
107. Zhang Z, Liu Y, Gong M, Zhao X, Zhang Y, Wang J (2010) Angew Chem Int Ed 49:1139-1142
108. Zhou L, Ye F, Zhang Y, Wang J (2010) J Am Chem Soc 132:13590-13591
109. Zhou L, Ye F, Ma J, Zhang Y, Wang J (2010) Angew Chem Int Ed 50:3510-3514