Nickel-catalyzed coupling of terminal allenes, aldehydes, and silanes

Tetrahedron

Volumn 62, Issue 49, 2006, Pages 11350-11359

  Ng, Sze Sze ^a   Jamison, Timothy F ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

Allene; Allylic alcohol; N Heterocyclic carbene; Nickel; Silane

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE; ALLENE DERIVATIVE; CARBENOID; NICKEL; PHOSPHINE DERIVATIVE; SILANE DERIVATIVE;

ARTICLE; CATALYSIS; PRIORITY JOURNAL;

EID: 33750487159     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.05.006     Document Type: Article

References (120)

1. In: Tamaru Y. (Ed). Modern Organonickel Chemistry (2005), Wiley-VCH, Weinheim
2. Alkyne:
3. Oblinger E., and Montgomery J. J. Am. Chem. Soc. 119 (1997) 9065-9066
4. Huang W.-S., Chan J., and Jamison T.F. Org. Lett. 2 (2000) 4221-4223
5. Colby E.A., and Jamison T.F. J. Org. Chem. 68 (2003) 126-166
6. Miller K.M., Huang W.-S., and Jamison T.F. J. Am. Chem. Soc. 125 (2003) 3442-3443
7. Molinaro C., and Jamison T.F. J. Am. Chem. Soc. 125 (2003) 8076-8077
8. Patel S.J., and Jamison T.F. Angew. Chem., Int. Ed. 42 (2003) 1364-1367
9. Mahandru G.M., Liu G., and Montgomery J. J. Am. Chem. Soc. 126 (2004) 3698-3699
10. Patel S.J., and Jamison T.F. Angew. Chem., Int. Ed. 43 (2004) 3941-3944
11. Kimura M., Ezoe A., Mori M., and Tamaru Y. J. Am. Chem. Soc. 127 (2005) 201-209
12. Knapp-Reed B., Mahandru G.M., and Montgomery J. J. Am. Chem. Soc. 127 (2005) 13156-13157
13. Luanphaisarnnont T., Ndubaku C.O., and Jamison T.F. Org. Lett. 7 (2005) 2937-2940 Enyne:
14. Miller K.M., and Jamison T.F. J. Am. Chem. Soc. 126 (2004) 15342-15343
15. Miller K.M., Luanphaisarnnont T., Molinaro C., and Jamison T.F. J. Am. Chem. Soc. 126 (2004) 4130-4131
16. Miller K.M., Colby E.A., Woodin K.S., and Jamison T.F. Adv. Synth. Catal. 347 (2005) 1533-1536
17. Miller K.M., and Jamison T.F. Org. Lett. 7 (2005) 3077-3080
18. Moslin R.M., and Jamison T.F. Org. Lett. 8 (2006) 455-458 Allene:
19. Takimoto M., Kawamura M., Mori M., and Sato Y. Synlett (2005) 2019-2022
20. Ng S.-S., and Jamison T.F. J. Am. Chem. Soc. 127 (2005) 7320-7321
21. Ng S.-S., and Jamison T.F. Tetrahedron 61 (2005) 11405-11417
22. Song M., and Montgomery J. Tetrahedron 61 (2005) 11440-11448 Alkene:
23. Ng S.-S., and Jamison T.F. J. Am. Chem. Soc. 127 (2005) 14194-14195 Diene:
24. Kimura M., Ezoe A., Shibata K., and Tamaru Y. J. Am. Chem. Soc. 120 (1998) 4033-4034
25. Kimura M., Fujimatsu H., Ezoe A., Shibata K., Shimizu M., Matsumoto S., and Tamaru Y. Angew. Chem., Int. Ed. 38 (1999) 397-400
26. Sato Y., Sawaki R., Saito N., and Mori M. J. Org. Chem. 67 (2002) 656-662
27. Sato Y., Takanashi T., Hoshiba M., and Mori M. J. Organomet. Chem. 688 (2003) 36-48
28. Takimoto M., Nakamura Y., Kimura K., and Mori M. J. Am. Chem. Soc. 126 (2004) 5956-5957
29. Sawaki R., Sato Y., and Mori M. Org. Lett. 6 (2004) 1131-1133
30. Takimoto M., Kajima Y., Sato Y., and Mori M. J. Org. Chem. 70 (2005) 8605-8606 Nickel-catalyzed reductive coupling review:
31. Montgomery J. Angew. Chem., Int. Ed. 43 (2004) 3890-3908
32. Jin H., Uenishi J., Christ W.J., and Kishi Y. J. Am. Chem. Soc. 108 (1986) 5644-5646
33. Takai K., Tagashira M., Kuroda T., Oshima K., Utimoto K., and Nozaki H. J. Am. Chem. Soc. 108 (1986) 6048-6050
34. Fürstner A., and Shi N. J. Am. Chem. Soc. 118 (1996) 2533-2534
35. Fürstner A., and Shi N. J. Am. Chem. Soc. 118 (1996) 12349-12357 Review:
36. Fürstner A. Chem. Rev. 99 (1999) 991-1045 Recent advance:
37. Namba K., Wang J., Cui S., and Kishi Y. Org. Lett. 7 (2005) 5421-5424 Asymmetric variants:
38. Choi H.-W., Nakajima K., Demeke D., Kang F.-A., Jun H.-S., Wan Z.-K., and Kishi Y. Org. Lett. 4 (2002) 4435-4438
39. Berkessel A., Menche D., Sklorz C.A., Schröder M., and Paterson I. Angew. Chem., Int. Ed. 42 (2003) 1032-1035
40. Namba K., and Kishi Y. Org. Lett. 6 (2004) 5031-5033
41. Namba K., Cui S., Wang J., and Kishi Y. Org. Lett. 7 (2005) 5417-5419
42. Recent review of catalytic asymmetric organozinc addition to carbonyl compounds:
43. Pu L., and Yu H.-B. Chem. Rev. 101 (2001) 757-824 Recent advances:
44. Chen Y.K., and Walsh P.J. J. Am. Chem. Soc. 126 (2004) 3702-3703
45. Li H., and Walsh P.J. J. Am. Chem. Soc. 127 (2005) 8355-8361
46. Review of recent advances on allene chemistry:
47. Ma S. Chem. Rev. 105 (2005) 2829-2872
48. Ha Y.-H., and Kang S.-K. Org. Lett. 4 (2002) 1143-1146
49. Montgomery J., and Song M. Org. Lett. 4 (2002) 4009-4011
50. Kang S.-K., and Yoon S.-K. Chem. Commun. (2002) 2634-2635
51. Kang S.-K., Kim K.-J., and Hong Y.-T. Angew. Chem., Int. Ed. 41 (2002) 1584-1586
52. Amarasinghe K.K.D., and Montgomery J. J. Am. Chem. Soc. 124 (2002) 9366-9367
53. Kang S.-K., Lee S.-W., Jung J., and Lim Y. J. Org. Chem. 67 (2002) 4376-4379
54. Kang S.-K., Ha Y.-H., Ko B.-S., Lim Y., and Jung J. Angew. Chem., Int. Ed. 41 (2002) 343-345
55. Kang S.-K., Hong Y.-T., Lee J.-H., Kim W.-Y., Lee I.-H., and Yu C.-M. Org. Lett. 5 (2003) 2813-2816
56. Kumareswaran R., Gallucci J., and RajanBabu T.V. J. Org. Chem. 69 (2004) 9151-9158 Allene-aldehyde couplings:
57. Trost B.M., Pinkerton A.B., and Seidel M. J. Am. Chem. Soc. 121 (1999) 10842-10843
58. Anwar U., Grigg R., Rasparini M., Savic V., and Sridharan V. Chem. Commun. (2000) 645-646
59. Anwar U., Grigg R., and Sridharan V. Chem. Commun. (2000) 933-934
60. Chang H.M., and Cheng C.H. Org. Lett. 2 (2000) 3439-3442
61. Liu G., and Lu X. Org. Lett. 3 (2001) 3879-3882
62. Trost B.M., Pinkerton A.B., and Seidel M. J. Am. Chem. Soc. 123 (2001) 12466-12476
63. Liu G., and Lu X. Tetrahedron Lett. 44 (2003) 127-130
64. Cleghorn L.A.T., Cooper I.R., Fishwick C.W.G., Grigg R., MacLachlan W.S., Rasparini M., and Sridharan V. J. Organomet. Chem. 687 (2003) 483-493
65. Cleghorn L.A.T., Cooper I.R., Grigg R., MacLachlan W.S., and Sridharan V. Tetrahedron Lett. 44 (2003) 7969-7973
66. Cleghorn L.A.T., Cooper I.R., Grigg R., MacLachlan W.S., and Sridharan V.J. Tetrahedron Lett. 44 (2004) 7969-7973
67. Hopkins C.D., and Malinakova H.C. Org. Lett. 6 (2004) 2221-2224
68. Hopkins C.D., Guan L., and Malinakova H.C. J. Org. Chem. 70 (2005) 6848-6862
69. See Refs. 2q, 2r, and 2t.
70. Pattenden G., and Robertson G.M. Tetrahedron Lett. 24 (1983) 4617-4620
71. Pattenden G., and Robertson G.M. Tetrahedron 41 (1985) 4001-4011
72. Crandall J.K., and Mualla M. Tetrahedron Lett. 27 (1986) 2243-2246
73. Gillmann T. Tetrahedron Lett. 34 (1993) 607-610
74. Holemann A., and Reissig H.-U. Org. Lett. 5 (2003) 1463-1466
75. Molander G.A., and Cormier E.P. J. Org. Chem. 70 (2005) 2622-2626
76. For examples, see Refs. 2v, 2d, 2e, and 2l.
77. Arduengo III A.J., Harlow R.L., and Kline M. J. Am. Chem. Soc. 113 (1991) 361-363
78. N-Heterocyclic carbene reviews:
79. Herrmann W.A. Angew. Chem., Int. Ed. 41 (2002) 1290-1309
80. Perry M.C., and Burgess K. Tetrahedron: Asymmetry 14 (2003) 951-961
81. César V., Bellemin-Laponnaz S., and Gade L.H. Chem. Soc. Rev. 33 (2004) 619-636 Recent advances:
82. Gstöttmayr C.W.K., Böhm W.P.W., Herdtweck E., Grosche M., and Herrmann W.A. Angew. Chem., Int. Ed. 41 (2002) 1363-1365
83. Navarro O., Kelly III R.A., and Nolan S.P. J. Am. Chem. Soc. 125 (2003) 16194-16195
84. Grubbs R.H. Tetrahedron 60 (2004) 7117-7140
85. Laitar D.S., Müller P., and Sadighi J.P. J. Am. Chem. Soc. 127 (2005) 17196-17197
86. Hadei N., Kantchev E.A.B., O'Brien C.J., and Organ M.G. J. Org. Chem. 70 (2005) 8503-8507
87. Vehlow K., Maechling S., and Blechert S. Organometallics 25 (2006) 25-28
88. Nucleophilic carbenes in organocatalysis: review:
89. Enders D., and Balensiefer T. Acc. Chem. Res. 37 (2004) 534-541
90. Grasa G.A., Singh R., and Nolan S.P. Synthesis 7 (2004) 971-985
91. Recent advances:
92. Coulembier O., Dove A.P., Pratt R.C., Sentman A.C., Culkin D.A., Mespouille L., Dubois P., Waymouth R.M., and Hedrick J.L. Angew. Chem., Int. Ed. 44 (2005) 4964-4968
93. Christmann M. Angew. Chem., Int. Ed. 44 (2005) 2632-2634
94. Nair V., Sreekumar V., Bindu S., and Suresh E. Org. Lett. 7 (2005) 2297-2300
95. Ye W., Cai G., Zhuang Z., Jia X., and Zhai H. Org. Lett. 7 (2005) 3769-3771
96. Chan A., and Scheidt K.A. Org. Lett. 7 (2005) 905-908
97. Read de Alaniz J., and Rovis T. J. Am. Chem. Soc. 127 (2005) 6284-6289
98. Myers M.C., Bharadwaj A.R., Milgram B.C., and Scheidt K.A. J. Am. Chem. Soc. 127 (2005) 14675-14680
99. Kano T., Sasaki K., and Maruoka K. Org. Lett. 7 (2005) 1347-1349
100. Movassaghi M., and Schmidt M.A. Org. Lett. 7 (2005) 2453-2456
101. Suzuki Y., Muramatsu K., Yamauchi K., Morie Y., and Sato M. Tetrahedron 62 (2005) 302-310
102. Fischer C., Smith S.W., Powell D.A., and Fu G.C. J. Am. Chem. Soc. 128 (2006) 1472-1473
103. Nair V., Vellalath S., Poonoth M., Mohan R., and Suresh E. Org. Lett. 8 (2006) 507-509
104. Theoretical calculation of the basicity of NHCs:
105. Magill A.M., Cavell K.J., and Yates B.F. J. Am. Chem. Soc. 126 (2004) 8717-8724 It has been demonstrated that a related alkyl carbene IAd (1,3-di-(1-adamantyl)-imidazol-2-ylidene) promoted the Claisen condensation of methyl acetate:
106. Grasa G.A., Singh R., Scott N.M., Stevens E.D., and Nolan S.P. Chem. Commun. (2004) 2890-2891
107. Examples of Ni/NHC catalyzed transformations:
108. Desmarets C., Kuhl S., Schneider R., and Fort Y. Organometallics 21 (2002) 1554-1559
109. Kuhl S., Schneider R., and Fort Y. Organometallics 22 (2003) 4184-4186
110. Ketz B.E., Ottenwaelder X.G., and Waymouth R.M. Chem. Commun. (2005) 5693-5695
111. Li W., Sun H., Chen M., Wang Z., Hu D., Shen Q., and Zhang Y. Organometallics 24 (2005) 5925-5928
112. Inamoto K., Kuroda J.-I., Danjo T., and Sakamoto T. Synlett (2005) 1624-1626
113. Duong H.A., Cross M.J., and Louie J. J. Am. Chem. Soc. 126 (2004) 11438-11439
114. Murakami M., Ashida S., and Matsuda T. J. Am. Chem. Soc. 128 (2006) 2166-2167
115. For examples, see Refs. 2g, 2j, and 10n.
116. For examples of Palladium-catalyzed enantioselective coupling of allenes and aldehydes see Refs. 5u and 5v.
117. Arduengo III A.J., Krafczyk R., and Schmutzler R. Tetrahedron 55 (1999) 14523-14534
118. Taherirastgar F., and Brandsma L. Synth. Commun. 27 (1997) 4035-4040
119. Myers A.G., and Zheng B. J. Am. Chem. Soc. 118 (1996) 4492-4493
120. Myers A.G., Zheng B., and Movassaghi M. J. Org. Chem. 62 (1997) 7507