Transition-metal-catalyzed additions of carbonyl functionalities to alkynes

Synlett

Volumn , Issue 17, 2010, Pages 2537-2548

  Fujihara, Tetsuaki ^a   Iwai, Tomohiro ^a   Terao, Jun ^a   Tsuji, Yasushi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

addition reactions; alkynes; annulations; iridium; palladium

Indexed keywords

ACID CHLORIDE; ALDEHYDE OXIDASE; ALKYNE DERIVATIVE; CARBONYL DERIVATIVE; CHLORIDE; DEUTERIUM; FORMAMIDE DERIVATIVE; IRIDIUM; PALLADIUM; RHODIUM; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

ADDITION REACTION; ANNULATION REACTION; CATALYSIS; CHEMICAL BOND; CHEMICAL INTERACTION; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; COMPLEX FORMATION; CONTROLLED STUDY; DECARBONYLATION; INTERMETHOD COMPARISON; LIGAND BINDING; REVIEW; STOICHIOMETRY; SYNTHESIS;

EID: 77958142824     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1258776     Document Type: Review

References (64)

1. Kollár K, Modern Carbonylation Methods Wiley-VCH Weinheim 2008
2. Beller M, Catalytic Carbonylation Reactions Springer Heidelberg 2006
3. Colquhoun H M., Thompson D J., Twigg M V., Carbonylation: Direct Synthesis of Carbonyl Compounds Plenum New York 1991
4. Morimoto T, Kakiuchi K, Angew. Chem. Int. Ed. 2004 43 5580
5. Sheldon R A., Pure Appl. Chem. 2000 72 1233
6. Trost B M., Acc. Chem. Res. 2002 35 695
7. Willis M C., Chem. Rev. 2010 110 725
8. Park Y J., Park J.-W, Jun C.-H, Acc. Chem. Res. 2008 41 222
9. Padwa A, Zhang H, J. Org. Chem. 2007 72 2570
10. Zhang H, Padwa A, Tetrahedron Lett. 2006 47 3905
11. Ikeda S, Shibuya M, Iwabuchi Y, Chem. Commun. 2007 504
12. Malerich J P., Maimone T J., Elliott G I., Trauner D, J. Am. Chem. Soc. 2005 127 6276
13. Harmata M, Wacharasindhu S, Org. Lett. 2005 7 2563
14. Weatherhead G S., Cortez G A., Schrock R R., Hoveyda A H., Proc. Natl. Acad. Sci. U.S.A. 2004 101 5805
15. Tsuji J, Ohno K, Tetrahedron Lett. 1965 6 3969
16. Ohno K, Tsuji J, J. Am. Chem. Soc. 1968 90 99
17. Doughty D H., Pignolet L H., J. Am. Chem. Soc. 1978 100 7083
18. Fristrup P, Kreis M, Palmelund A, Norrby P, Madsen R, J. Am. Chem. Soc. 2008 130 5206
19. Kreis M, Palmelund A, Bunch L, Madsen R, Adv. Synth. Catal. 2006 348 2148
20. Iwai T, Fujihara T, Tsuji Y, Chem. Commun. 2008 6215
21. Abu-Hasanayn F, Goldman M E., Goldman A S., J. Am. Chem. Soc. 1992 114 2520
22. Pohland A E., Benson W R., Chem. Rev. 1966 66 161
23. Zhou H, Zeng C, Ren L, Liao W, Huang X, Synlett 2006 3504
24. Martens H, Janssens F, Hoornaert G, Tetrahedron 1975 31 177
25. Price C C., Pappalardo [nl]J A., J. Am. Chem. Soc. 1950 72 2613
26. Wang B, Wang S, Li P, Wang L, Chem. Commun. 2010 46 5891
27. Collman J P., Hegedus L S., Norton J R., Finke R G., Principles and Applications of Organotransition Metal Chemistry University Science Books Mill Valley 1987 Chap. 5
28. Kokubo K, Matsumasa K, Miura M, Nomura M, J. Org. Chem. 1996 61 6941
29. Kashiwabara T, Fuse K, Hua R, Tanaka M, Org. Lett. 2008 10 5469
30. Kashiwabara T, Kataoka K, Hua R, Shimada S, Tanaka M, Org. Lett. 2005 7 2241
31. N-Heterocyclic Carbenes in Synthesis Nolan S P. Wiley-VCH Weinheim 2006
32. Iwai T, Fujihara T, Terao J, Tsuji Y, J. Am. Chem. Soc. 2009 131 6668
33. Martin R, Buchwald S L., Acc. Chem. Res. 2008 41 1461
34. Lee K Y., Lee M J., Kim J N., Tetrahedron 2005 61 8705
35. Zhang M, Jiang H.-F, Neumann H, Beller M, Dixneuf P H., Angew. Chem. Int. Ed. 2009 48 1681
36. Dudnik A S., Sromek A W., Rubina M, Kim J T., Kelin A V., Gevorgyan V, J. Am. Chem. Soc. 2008 130 1440; and references cited therein
37. Tsuji Y, Yoshii S, Ohsumi T, Kondo T, Watanabe Y, J. Organomet. Chem. 1987 331 379
38. Kondo T, Okada T, Mitsudo T, Organometallics 1999 18 4123
39. Ko S, Han H, Chang S, Org. Lett. 2003 5 2687
40. Kobayashi Y, Kamisaki H, Yanada K, Yanada R, Takemoto Y, Tetrahedron Lett. 2005 46 7549
41. Nakao Y, Idei H, Kanyiva K S., Hiyama T, J. Am. Chem. Soc. 2009 131 5070
42. Fujihara T, Katafuchi Y, Iwai T, Terao J, Tsuji Y, [nl]J. Am. Chem. Soc. 2010 132 2094
43. Hills I D., Fu G C., J. Am. Chem. Soc. 2004 126 13178
44. Grushin V V., Chem. Rev. 1996 96 2011
45. Kudo K, Hidai M, Murayama T, Uchida Y, J. Chem. Soc. D 1970 1701
46. Lindhardt A T., Mantel M L. H., Skrydstrup T, Angew. Chem. Int. Ed. 2008 47 2668
47. Park J H., Kim S Y., Kim S M., Chung Y K., Org. Lett. 2007 9 2465
48. Li Y, Alper H, Yu Z, Org. Lett. 2006 8 5199
49. Negishi E, In Organopalladium Chemistry for Organic Synthesis Negishi E deMeijere A Wiley-Interscience New York 2002 135-137
50. Canty A J., Acc. Chem. Res. 1992 25 86
51. Eicher T, Hauptmann S, The Chemistry of Heterocycles Wiley-VCH Weinheim 2003
52. Costero A M., Advances in Heterocyclic Chemistry 1993 58 171
53. Guimond N, Gouliaras C, Fagnou K, J. Am. Chem. Soc. 2010 132 6908
54. Kajita Y, Matsubara S, Kurahashi T, J. Am. Chem. Soc. 2008 130 6058
55. Kajita Y, Kurahashi T, Matsubara S, J. Am. Chem. Soc. 2008 130 17226
56. Yoshino Y, Kurahashi T, Matsubara S, J. Am. Chem. Soc. 2009 131 7494
57. Miura T, Yamauchi M, Murakami M, Org. Lett. 2008 10 3085
58. Lemoucheux L, Rouden J, Ibazizene M, Sobrio F, Lasne M.-C, J. Org. Chem. 2003 68 7289
59. Kochi T, Urano S, Seki H, Mizushima E, Sato M, Kakiuchi F, J. Am. Chem. Soc. 2009 131 2792
60. Yasui Y, Takemoto Y, Chem. Rec. 2008 8 386
61. Yasui Y, Kakinokihara I, Takeda H, Takemoto Y, Synthesis 2009 3989
62. Iwai T, Fujihara T, Terao J, Tsuji Y, J. Am. Chem. Soc. 2010 132 9602
63. Hiwatari K, Kayaki Y, Okita K, Ukai T, Shimizu I, Yamamoto A, Bull. Chem. Soc. Jpn. 2004 77 2237; and references cited therein
64. Rahim M, Bushweller H, Ahmed K J., Organometallics 1994 13 4952