N,N-Dimethylformamide: much more than a solvent

Tetrahedron

Volumn 65, Issue 40, 2009, Pages 8313-8323

  Muzart, Jacques ^a  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

Author keywords

Amidation; Aminocarbonylation; Carbonylation; Catalysis; Cycloaddition; Dehydration; DMF; Formylation; N,N Dimethylformamide; Reduction

Indexed keywords

ALDOXIME; ALKENE DERIVATIVE; CARBON MONOXIDE; COPPER; DIMETHYLAMINE; EPOXIDE; FORMIC ACID; HALIDE; MESYLIC ACID DERIVATIVE; MORPHOLINE; N,N DIMETHYLFORMAMIDE; ORGANOLITHIUM COMPOUND; OXYGEN; PALLADIUM; REDUCING AGENT; SILANE DERIVATIVE; SILVER; SOLVENT; TOLUENESULFONIC ACID DERIVATIVE;

ADDITION REACTION; AMIDATION; AMINATION; CARBAMOYLATION; CARBONYLATION; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; DECOMPOSITION; ELIMINATION REACTION; FORMYLATION; ISOMERIZATION; PRIORITY JOURNAL; REDUCTION; REVIEW; SOLVENT EFFECT; SUBSTITUTION REACTION;

EID: 69249248122     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.06.091     Document Type: Review

References (145)

1. Gutmann V. Coordination Chemistry in Non-aqueous Solutions (1968), Springer, Wien pp 152-154
2. Hosokawa T., Nomura T., and Murahashi S.-I. J. Organomet. Chem. 551 (1998) 387-389
3. Jutand A. Eur. J. Inorg. Chem. (2003) 2017-2040
4. Aresta M., Pastore C., Giannoccaro P., Kovács G., Dibenedetto A., and Pápai I. Chem.-Eur. J. 13 (2007) 9028-9034
5. Jutand A. Chem. Rev. 108 (2008) 2300-2347
6. Álvarez R., Pérez M., Faza O.N., and de Lera A.R. Organometallics 27 (2008) 3378-3389
7. Amatore C., Jutand A., Meyer G., Carelli I., and Chiarotto I. Eur. J. Inorg. Chem. (2000) 1855-1859
8. Kuhn S.J., and McIntyre J.S. Can. J. Chem. 43 (1965) 995-998
9. Gore E.S., Blears D.J., and Danyluk S.S. Can. J. Chem. 43 (1965) 2135-2140
10. Clayden J., Greeves N., Warren S., and Wothers P. Organic Chemistry (2001), Oxford University Press, Oxford p 1158
11. Jutz C. In: Taylor E.C. (Ed). Advances in Organic Chemistry Vol. 9 (1976), Wiley, J, New York, NY 225-342
12. Meth-Cohn O., and Stanforth S.P. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 2 (1991), Pergamon, London 777-794
13. Marson C.M. Tetrahedron 48 (1992) 3659-3726
14. Jones G., and Stanforth S.P. In: Paquette L.A. (Ed). Organic Reactions Vol. 49 (1997), Wiley, New York, NY 1-330
15. Gilles P.R., and Marson C.M. In: Coates R.M., and Denmark S.E. (Eds). Handbook of Reagents for Organic Synthesis; Reagents, Auxiliaries, and Catalysts for C-C Bond Formation (1999), Wiley, Chichester, UK 309-312
16. Comins D.L., and Joseph S.P. In: Coates R.M., and Denmark S.E. (Eds). Handbook of Reagents for Organic Synthesis; Reagents, Auxiliaries, and Catalysts for C-C Bond Formation (1999), Wiley, Chichester, UK 312-315
17. Jones G., and Stanforth S.P. In: Overman L.O. (Ed). Organic Reactions Vol. 56 (2000), Wiley, New York, NY 355-659
18. Brahma S., and Ray J.K. Tetrahedron 64 (2008) 2883-2896
19. For the Wacker reaction, see:. Tsuji J. Synthesis (1984) 369-384
20. For recent examples, see:
21. Kiyooka S., Matsumoto S., Kojima M., Sakonaka K., and Maeda H. Tetrahedron Lett. 49 (2008) 1589-1592
22. Majumdar K.C., Chattopadhyay B., and Nath S. Tetrahedron Lett. 49 (2008) 1609-1612
23. Zhong W., Liu Z., Yu C., and Su W. Synlett (2008) 2888-2892
24. Huang H., Liu H., Jiang H., and Chen K. J. Org. Chem. 73 (2008) 6037-6040
25. Wu M., Mao J., Guo J., and Ji S. Eur. J. Org. Chem. (2008) 4050-4054
26. Chaumontet M., Piccardi R., Audic N., Hitce J., Peglion J.-L., Clot E., and Baudoin O. J. Am. Chem. Soc. 130 (2008) 15157-15166
27. Tu S.-J., Yan S., Cao X.-D., Wu S.-S., Zhang X.-H., Hao W.-J., Han Z.-G., and Shi F. J. Organomet. Chem. 694 (2008) 91-96
28. Jana R., Chatterjee I., Samanta S., and Ray J.K. Org. Lett. 10 (2008) 4795-4797
29. Majumdar K.C., Chattopadhyay B., and Sinha B. Synthesis (2008) 3857-3863
30. Luo H.-Q., and Loh T.-P. Tetrahedron Lett. 50 (2009) 1554-1556
31. Majumdar K.C., Sinha B., Maji P.K., and Chattopadhyay S.K. Tetrahedron 65 (2009) 2751-2756
32. Kobayashi K., and Kondo Y. Org. Lett. 11 (2009) 2035-2037
33. Hagiwara H., Iijima D., Awen B.Z.S., Hoshi T., and Suzuki T. Synlett (2008) 1520-1522
34. Alcaide B., Almendros P., Martínez del Campo T., and Carrascoa R. Chem. Asian J. 3 (2008) 1140-1145
35. Zawisza A.M., Bouquillon S., and Muzart J. Eur. J. Org. Chem. (2007) 3901-3904
36. Evans L.A., Fey N., Harvey J.N., Hose D., Lloyd-Jones G.C., Murray P., Orpen A.G., Osborne R., Owen-Smith G.J.J., and Purdie M. J. Am. Chem. Soc. 130 (2008) 14471-14473
37. For a recent report on the solvent-depending shape of reaction profiles, see:. van Bochove M.A., and Bikelhaupt F.M. Eur. J. Org. Chem. (2008) 649-654
38. Parker A.J. Chem. Rev. 69 (1969) 1-32
39. For a recent study, see:. Amatore C., Catellani M., Deladda S., Jutand A., and Motti E. Organometallics 27 (2008) 4549-4554
40. Amatore C., Jutand A., Meyer G., and Mottier L. Chem.-Eur. J. 5 (1999) 466-473
41. Bouquillon S., and Muzart J. Eur. J. Org. Chem. (2001) 3301-3305
42. Amatore C., Jutand A., and Mottier L. Eur. J. Inorg. Chem. (1999) 1081-1085
43. Narahashi H., Shimizu I., and Yamamoto A. J. Organomet. Chem. 693 (2008) 283-296
44. See also:. Ludwig M., Strömberg S., Svensson M., and Åkermark B. Organometallics 18 (1999) 970-975
45. Kovala-Demertzi D., Kourkoumelis N., West D.X., Valdés-Martínez J., and Hernández-Ortega S. Eur. J. Inorg. Chem. (1998) 861-863
46. Sugawara Y., Yamada W., Yoshida S., Ikeno T., and Yamada T. J. Am. Chem. Soc. 129 (2007) 12902-12903
47. De Kimpe N., De Buyck L., Verhe R., Wychuyse F., and Schamp N. Synth. Commun. 9 (1979) 575-592
48. Jiang J.-L., Xiu Z., and Hua R. Synth. Commun. 38 (2008) 232-238
49. Satgé C., Le Bras J., Hénin F., and Muzart J. Tetrahedron 61 (2005) 8405-8409
50. Nishida Y., Shingu Y., Dohi H., and Kobayashi K. Org. Lett. 5 (2003) 2377-2380
51. Kobayashi S., and Nishio K. Tetrahedron Lett. 34 (1993) 3453-3456
52. Kobayashi S., and Nishio K. J. Org. Chem. 5967 (1994) 6620-6628
53. Kobayashi S., and Hirabayashi R. J. Am. Chem. Soc. 121 (1999) 6942-6943
54. Ogawa C., Sugiura M., and Kobayashi S. J. Org. Chem. 67 (2002) 5359-5364
55. Hirabayashi R., Ogawa C., Sugiura M., and Kobayashi S. J. Am. Chem. Soc. 123 (2001) 9493-9499
56. Ogawa C., Sugiura M., and Kobayashi S. Synlett (2003) 1749-1751
57. Wu P., and Sun J. Synth. Commun. 38 (2008) 1003-1010
58. Perrin D.D., Armarego W.L.F., and Perrin D.R. Purification of Laboratory Chemicals (1966), Pergamon, Oxford p 143
59. Rusina A., and Vlček A.A. Nature 206 (1965) 295-296
60. Serp P., Hernandez M., Richard B., and Kalck P. Eur. J. Inorg. Chem. (2001) 2327-2336 This report contains an informative short survey of the literature on the reactions of DMF with metal complexes
61. Serp P., Hernandez M., and Kalck P. C. R. Acad. Sci. Paris, Série IIc: Chimie 2 (1999) 267-272
62. Coalter III J.N., Huffman J.C., and Caulton K.G. Organometallics 19 (2000) 3569-3578
63. Tsuji J., and Mandai T. Synthesis (1996) 1-24
64. Wu X., Mahalingam A.K., Wan Y., and Alterman M. Tetrahedron Lett. 45 (2004) 4635-4638
65. Coppinger G.M. J. Am. Chem. Soc. 76 (1954) 1372-1373
66. Balogh-Hergovich E., and Speier G. J. Chem. Soc., Chem. Commun. (1991) 551-552
67. Balogh-Hergovich E., Kaizer J., and Speier G. J. Mol. Catal. A: Chem. 159 (2000) 215-224
68. Balogh-Hergovich E., Kaizer J., Speier G., Huttner G., and Jacobi A. Inorg. Chem. 39 (2000) 4224-4229
69. March J. Advanced Organic Chemistry. 2nd ed. (1977), McGraw-Hill Book, New York, NY p 383
70. Kadish K.M., Han B.C., Franzen M.M., and Araullo-McAdams C. J. Am. Chem. Soc. 112 (1990) 8364-8368
71. Agarwal A., and Chauhan P.M.S. Synth. Commun. 34 (2004) 2925-2930
72. Heindel N.D., and Kennewell P.D. Chem. Commun. (1969) 38
73. Watanabe T., Tanaka Y., Sekiya K., Akita Y., and Ohta A. Synthesis (1980) 39-41
74. D'Amico J.J., Webster S.T., Campbell R.H., and Twine C.E. J. Org. Chem. 30 (1965) 3618-3625
75. Sharma A., Mehta V.P., and Van der Eycken E. Tetrahedron 64 (2008) 2605-2610
76. Cho Y.H., and Park J.C. Tetrahedron Lett. 38 (1997) 8331-8334
77. Nasipuri D., Bhattacharyya A., and Hazra B.G. J. Chem. Soc., Chem. Commun. (1971) 660-661
78. Powers J.C., Seidner R., and Parsons T.G. Tetrahedron Lett. (1965) 1713-1716
79. Paul S., and Schmidt R.R. Synlett (2002) 1107-1108
80. Filali E., Lloyd-Jones G., and Sale D.A. Synlett (2009) 205-208
81. Toffano M., Legros J.-Y., and Fiaud J.-C. Tetrahedron Lett. 38 (1997) 77-80
82. Malkhasian A.Y.S., Finch M.E., Nikolovski B., Menon A., Kucera B.E., and Chavez F.A. Inorg. Chem. 46 (2007) 2950-2952
83. For the accurate structure of the Cu catalyst, see:. Warden A.C., Spiccia L., Hearn M.T.W., Boas J.F., and Pilbrow J.R. J. Chem. Soc., Dalton Trans. (2005) 1804-1813
84. Wan Y., Alterman M., Larhed M., and Hallberg A. J. Org. Chem. 67 (2002) 6232-6235
85. Wayland B.B., and Schramm R.F. Inorg. Chem. 8 (1969) 971-976
86. Teo J.J., Chang Y., and Zeng H.C. Langmuir 22 (2006) 7369-7377
87. Pastoriza-Santos I., and Liz-Marzán L.M. Nano Lett. 2 (2002) 903-905
88. Sharma J., Mahima S., Kakade B.A., Pasricha R., Mandale A.B., and Vijayamohanan K. J. Phys. Chem. B 108 (2004) 13280-13286
89. Pletnev A.A., Tian Q., and Larock R.C. J. Org. Chem. 67 (2002) 9276-9287
90. Cacchi S., Felici M., and Pietroni B. Tetrahedron Lett. 25 (1984) 3137-3140
91. Penalva V., Lavenot L., Gozzi C., and Lemaire M. Appl. Catal. A: Gen. 182 (1999) 399-405
92. McCrindle R., Ferguson G., Arsenault G.J., and McAlees A.J. J. Chem. Soc., Chem. Commun. (1983) 571-572
93. McCrindle R., Ferguson G., Arsenault G.J., McAlees A.J., and Stephenson D.K. J. Chem. Res., Synop. (1984) 360-361
94. J. Chem. Res., Miniprint (1984) 3301-3344
95. Trzeciak A.M., Ciunik Z., and Ziółkowski J.J. Organometallics 21 (2002) 132-137
96. Grushin V.V., and Alper H. Organometallics 12 (1993) 1890-1901
97. El Kaïm L., Gamez-Montaňo R., Grimaud L., and Ibarra-Rivera T. Chem. Commun. (2008) 1350-1352
98. Zawisza A.M., Ganchegui B., González I., Bouquillon S., Roglans A., Hénin F., and Muzart J. J. Mol. Catal. A: Chem. 283 (2008) 140-145
99. Zawisza A.M., and Muzart J. Tetrahedron Lett. 48 (2007) 6738-6742
100. Brenda M., Knebelkamp A., Greiner A., and Heitz W. Synlett (1991) 809-810
101. Legros J.-Y., Primault G., Toffano M., Rivière M.-A., and Fiaud J.-C. Org. Lett. 4 (2000) 433-436
102. Satyanarayana G., and Maier M.E. J. Org. Chem. 73 (2008) 5410-5415
103. Kim H.S., Gowrisankar S., Kim S.H., and Kim J.N. Tetrahedron Lett. 49 (2008) 3858-3861
104. Kim H.S., Lee H.S., Kim S.H., and Kim J.N. Tetrahedron Lett. 50 (2009) 3154-3157
105. See also Alterman's report.
106. Zask A., and Helquist P. J. Org. Chem. 43 (1978) 1619-1620
107. Lassová L., Lee H.K., and Hor T.S.A. J. Mol. Catal. A: Chem. 144 (1999) 397-403
108. 73 has been recently used for the dehalogenation of a vinyl bromide:. Taniguchi N. Synlett (2008) 849-852
109. Jin C.H., Lee H.Y., Lee S.H., Kim I.S., and Jung Y.H. Synlett (2007) 2695-2698
110. Serieys A., Botuha C., Chemla F., Ferreira F., and Pérez-Luna A. Tetrahedron Lett. 49 (2008) 5322-5323
111. Angyal S.J., and Odier L. Carbohydr. Res. 80 (1980) 203-206
112. Serrano P., Llebaria A., and Delgado A. J. Org. Chem. 70 (2005) 7829-7840
113. Boerwinkle F., and Hassner A. Tetrahedron Lett. (1968) 3921-3924
114. Dalton D.R., Smith Jr. J.R., and Jones D.G. Tetrahedron 26 (1970) 575-581
115. Pettit G.R., and Thomas E.G. J. Org. Chem. 24 (1959) 895-896
116. Kraus M.A. Synthesis (1973) 361-362
117. March J. Advanced Organic Chemistry. 4th ed. (1992), McGraw-Hill Book, New York, NY p 640
118. Otsuji Y., Matsumura N., and Imoto E. Bull. Chem. Soc. Jpn. 41 (1968) 1485
119. Takahashi K., Shibagaki M., and Matsushita H. Agric. Biol. Chem. 52 (1988) 853-854
120. Iwata M., and Kuzuhara H. Chem. Lett. 11 (1989) 2029-2030
121. Corey E.J., and Seebach D. Angew. Chem., Int. Ed. Engl. 4 (1965) 1077-1078
122. Khanapure S.P., Manna S., Rokach J., Murphy R.C., Wheelan P., and Powell W.S. J. Org. Chem. 60 (1995) 1806-1813
123. Groth U., Köttgen P., Langenbach P., Lindenmaier A., Schütz T., and Wiegand M. Synlett (2008) 1301-1304
124. Narasimhan N.S., Mali R.S., and Barve M.V. Synthesis (1979) 906-909
125. Kumar S., Jaller D., Patel B., LaLonde J.M., DuHadaway J.B., Malachowski W.P., Prendergast G.C., and Muller A.J. J. Med. Chem. 51 (2008) 4968-4977
126. Pizzuti M.B., Minnaard A.J., and Feringa B.L. Org. Biomol. Chem. 6 (2008) 3464-3466
127. Johansson M.J., Andersson K.H.O., and Kann N. J. Org. Chem. 73 (2008) 4458-4463
128. Engels R., and Schäfer H.J. Angew. Chem., Int. Ed. Engl. 17 (1978) 460
129. Young C.A., and Dewald R.D. J. Am. Chem. Soc. 101 (1979) 2884-2888
130. Botteghi C., Gotta S., Marchetti M., and Melloni G. Tetrahedron Lett. 33 (1992) 5601-5602
131. Chang F.C., and Blickenstaff R.T. J. Am. Chem. Soc. 80 (1958) 2906
132. Dakanali M., Tsikalas G.K., Krautscheid H., and Katerinopoulos H.E. Tetrahedron Lett. 49 (2008) 1648-1651
133. Corriu R.J.P., Moreau J.J.E., and Pataud-Sat M. J. Org. Chem. 55 (1990) 2878-2884
134. Tomashenko O., Sokolov V., Tomashevskiy A., Buchholz H.A., Welz-Biermann U., Chaplinski V., and de Meijere A. Eur. J. Org. Chem. (2008) 5107-5111
135. Minisci F., Citterio A., Vismara E., and Giordano C. Tetrahedron 41 (1985) 4157-4170
136. Kamiya I., Tsunoyama H., Tsukuda T., and Sakurai H. Chem. Lett. 36 (2007) 646-647
137. For a review on the Au-catalysed reactions of hydroxyalkenes, see:. Muzart J. Tetrahedron 64 (2008) 5815-5849
138. Liebscher J., and Hartmann H. Zeitschrift für Chemie 15 (1975) 302
139. Supsana P., Liaskopoulos T., Tsoungas P.G., and Varvounis G. Synlett (2007) 2671-2674
140. D'Angeli F., Cavicchioni G., Catelani G., Marchetti P., and Maran F. Gazz. Chim. Ital. 119 (1989) 471-474
141. Scrimain P., D'Angeli F., Veronese A.C., and Baiono V. Tetrahedron Lett. 24 (1983) 4473-4476
142. Maran F., Vianello E., Cavicchioni G., and D'Angeli F. J. Chem. Soc., Chem. Commun. (1985) 660-661
143. Maran F., Vianello E., D'Angeli F., Cavicchioni G., and Vecchiati G. J. Chem. Soc., Perkin Trans. 2 (1987) 33-38
144. Hanack M., and Wilhelm B. Angew. Chem., Int. Ed. Engl. 28 (1989) 1057-1059
145. Sanz R., Guilarte V., and Pérez A. Tetrahedron Lett. 50 (2009) 4423-4426