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DOI: 10.1055/s-0031-1290350
Molybdenum Hexacarbonyl Mediated CO Gas-Free Carbonylative Reactions
Publication History
Publication Date:
10 February 2012 (online)
Abstract
This Account summarizes predominately our own experiences in developing microwave-heated palladium-catalyzed Mo(CO)6-mediated gas-free carbonylative reactions, although contributions from other groups, including non-palladium-catalyzed examples, have also been covered. Presented reactions include amino-, amido-, and alkoxycarbonylations as well as carbonylative cyclizations and carbonylative cross-couplings, using Mo(CO)6 as a solid source of CO. The methodology was developed mainly for rapid small-scale applications, avoiding the problematic use of gaseous CO in a standard laboratory. In most cases, the reported Mo(CO)6-mediated carbonylations were conducted in sealed vessels and with reaction times of less than 1 hour. The Account also highlights relevant applications in medicinal and high-speed chemistry.
1 Introduction
2 Mo(CO)6-Promoted Carbonylations - The Beginning
3 Aminocarbonylations
4 Amidocarbonylations
5 Alkoxy- and Hydroxycarbonylations
6 Carbonylative Ring Closing of Aryl Halides
7 Carbonylative Cross-Couplings
8 Palladium-Free Mo(CO)6-Promoted Carbonylations
9 Summary and Outlook
Key words
carbonylation - molybdenum - multicomponent reaction - palladium - catalysis
-
1a
Schoenberg A.Bartoletti I.Heck RF. J. Org. Chem. 1974, 39: 3318 -
1b
Schoenberg A.Heck RF. J. Org. Chem. 1974, 39: 3327 -
2a
Beller M.Cornils B.Frohning CD.Kohlpaintner CW. J. Mol. Catal. A: Chem. 1995, 104: 17 -
2b
Skolda-Foldes R.Kollar L. Curr. Org. Chem. 2002, 6: 1097 -
2c
Barnard CFJ. Organometallics 2008, 27: 5402 -
2d
Modern
Carbonylation Methods
Kollár L. Wiley-VCH; Weinheim: 2008. -
2e
Brennführer A.Neumann H.Beller M. Angew. Chem. Int. Ed. 2009, 48: 4114 -
2f
Grigg R.Mutton SP. Tetrahedron 2010, 66: 5515 -
2g
Wu X.-F.Neumann H.Beller M. Chem. Soc. Rev. 2011, 40: 4986 -
4a
Morimoto T.Kakiuchi K. Angew. Chem. Int. Ed. 2004, 43: 5580 -
4b
Hermange P.Gøgsig TM.Lindhardt AT.Taaning RH.Skrydstrup T. Org. Lett. 2011, 13: 2444 -
4c
Hermange P.Lindhardt AT.Taaning RH.Bjerglund K.Lupp D.Skrydstrup T. J. Am. Chem. Soc. 2011, 133: 6061 - 5
Grushin VV.Alper H. Organometallics 1993, 12: 3846 -
6a
Hosoi K.Nozaki K.Hiyama T. Org. Lett. 2002, 4: 2849 -
6b
Wan Y.Alterman M.Larhed M.Hallberg A. J. Org. Chem. 2002, 67: 6232 -
6c
Wan Y.Alterman M.Larhed M.Hallberg A. J. Comb. Chem. 2003, 5: 82 -
6d
Schareina T.Zapf A.Cotté A.Gotta M.Beller M. Adv. Synth. Catal. 2010, 352: 1205 -
6e
Sawant DN.Wagh YS.Bhatte KD.Bhanage BM. J. Org. Chem. 2011, 76: 5489 -
7a
Morimoto T.Fuji K.Tsutsumi K.Kakiuchi K. J. Am. Chem. Soc. 2002, 124: 3806 -
7b
Shibata T.Toshida N.Takagi K. J. Org. Chem. 2002, 67: 7446 -
7c
Shibata T.Toshida N.Takagi K. Org. Lett. 2002, 4: 1619 - 8
Rao MLN.Venkatesh V.Dasgupta P. Tetrahedron Lett. 2010, 51: 4975 - 9
Caldirola P.Chowdhury R.Johansson AM.Hacksell U. Organometallics 1995, 14: 3897 -
10a
Strauss C.Trainor R. Aust. J. Chem. 1995, 48: 1665 -
10b
Ersmark K.Larhed M.Wannberg J. Curr. Opin. Drug Disc. 2004, 7: 417 -
10c
Kappe CO. Angew. Chem. Int. Ed. 2004, 43: 6250 -
10d
Larhed M.Wannberg J.Hallberg A. QSAR Comb. Sci. 2007, 26: 51 -
11a
Trost BM.Hachiya I. J. Am. Chem. Soc. 1998, 120: 1104 -
11b
Trost BM.Hildbrand S.Dogra K. J. Am. Chem. Soc. 1999, 121: 10416 -
11c
Glorius F.Pfaltz A. Org. Lett. 1999, 1: 141 -
12a
Belda O.Kaiser N.-F.Bremberg U.Larhed M.Hallberg A.Moberg C. J. Org. Chem. 2000, 65: 5868 -
12b
Kaiser N.-FK.Bremberg U.Larhed M.Moberg C.Hallberg A. Angew. Chem. Int. Ed. 2000, 39: 3595 - 13
Armarego WLF.Perrin DD. Purifications of Laboratory Chemicals Butterworth-Heinemann; Oxford: 1997. - 14
Kaiser NFK.Hallberg A.Larhed M. J. Comb. Chem. 2002, 4: 109 - 15
Herrmann WA.Brossmer C.Reisinger C.-P.Riermeier TH.Öfele K.Beller M. Chem. Eur. J. 1997, 3: 1357 - 16
Wannberg J.Larhed M. J. Org. Chem. 2003, 68: 5750 - 17
Yamazaki K.Kondo Y. J. Comb. Chem. 2004, 6: 121 - 18
Wannberg J.Dallinger D.Kappe CO.Larhed M. J. Comb. Chem. 2005, 7: 574 - 19
Netherton MR.Fu GC. Org. Lett. 2001, 3: 4295 - 20
Glasnov TN.Stadlbauer W.Kappe CO. J. Org. Chem. 2005, 70: 3864 -
21a
Nöteberg D.Schaal W.Hamelink E.Vrang L.Larhed M. J. Comb. Chem. 2003, 5: 456 -
21b
Wannberg J.Ersmark K.Larhed M. Top. Curr. Chem. 2006, 266: 167 - 22
Wannberg J.Kaiser N.-FK.Vrang L.Samuelsson B.Larhed M.Hallberg A. J. Comb. Chem. 2005, 7: 611 - 23
Lagerlund O.Larhed M. J. Comb. Chem. 2006, 8: 4 - 24
Wu X.Larhed M. Org. Lett. 2005, 7: 3327 - 25
Wu X.Ekegren JK.Larhed M. Organometallics 2006, 25: 1434 - 26
Gold H.Ax A.Vrang L.Samuelsson B.Karlén A.Hallberg A.Larhed M. Tetrahedron 2006, 62: 4671 - 27
Wu X.Wannberg J.Larhed M. Tetrahedron 2006, 62: 4665 - 28
Marradi M. Synlett 2005, 1195 ; and references therein - 29
Iizuka M.Kondo Y. Chem. Commun. 2006, 1739 - 30
Letavic MA.Ly KS. Tetrahedron Lett. 2007, 48: 2339 - 31
Begouin A.Queiroz M.-JRP. Eur. J. Org. Chem. 2009, 2820 - 32
Odell LR.Sävmarker J.Larhed M. Tetrahedron Lett. 2008, 49: 6115 - 33
Lagerlund O.Mantel MLH.Larhed M. Tetrahedron 2009, 65: 7646 - 34
Wieckowska A.Fransson R.Odell LR.Larhed M.
J. Org. Chem. 2011, 76: 978 - 35
Herrero MA.Wannberg J.Larhed M. Synlett 2004, 2335 -
36a
Wan Y.Wallinder C.Plouffe B.Beaudry H.Mahalingam AK.Wu X.Johansson B.Holm M.Botoros M.Karlén A.Pettersson A.Nyberg F.Fändriks L.Gallo-Payet N.Hallberg A.Alterman M. J. Med. Chem. 2004, 47: 5995 -
36b
Rönn R.Sabnis YA.Gossas T.Akerblom E.Helena Danielson U.Hallberg A.Johansson A. Bioorg. Med. Chem. 2006, 14: 544 - 37
Wu X.Rönn R.Gossas T.Larhed M. J. Org. Chem. 2005, 70: 3094 - 38
Rönn R.Lampa A.Peterson SD.Gossas T.Akerblom E.Danielson UH.Karlén A.Sandström A. Bioorg. Med. Chem. 2008, 16: 2955 - 39
Liptrot D.Alcaraz L.Roberts B. Tetrahedron Lett. 2010, 51: 5341 - 40
Liptrot D.Alcaraz L.Roberts B. Adv. Synth. Catal. 2010, 352: 2183 - 41
Georgsson J.Hallberg A.Larhed M. J. Comb. Chem. 2003, 5: 350 - 42
Georgsson J.Sköld C.Plouffe B.Lindeberg G.Botros M.Larhed M.Nyberg F.Gallo-Payet N.Gogoll A.Karlén A.Hallberg A. J. Med. Chem. 2005, 48: 6620 - 43 Gising, J.; Nilsson, M. T.; Odell,
L. R.; Yahiaoui, S.; Lindh, M.; Iyer, H.; Srinivasa, B. R.; Larhed,
M.; Mowbray, S. L.; Karlén, A. submitted
- 44
Odell LR.Nilsson MT.Gising J.Lagerlund O.Muthas D.Nordqvist A.Karlén A.Larhed M. Bioorg. Med. Chem. Lett. 2009, 19: 4790 - 45
Lesma G.Sacchetti A.Silvani A. Synthesis 2006, 594 - 46
Wu X.Nilsson P.Larhed M. J. Org. Chem. 2005, 70: 346 - 47
Gagnier SV.Larock RC. J. Am. Chem. Soc. 2003, 125: 4804 - 48
Cabri W.Candiani I.Bedeschi A.Santi R. J. Org. Chem. 1992, 57: 3558 - 49
Cao H.Xiao W.-J. Can. J. Chem. 2005, 83: 826 - 50
Chen J.-R.Liao J.Xiao W.-J. Can. J. Chem. 2010, 88: 331 - 51
Lindh J.Fardost A.Almeida M.Nilsson P. Tetrahedron Lett. 2010, 51: 2470 - 52
Sävmarker J.Lindh J.Nilsson P. Tetrahedron Lett. 2010, 51: 6886 - 53
Jafarpour F.Rashidi-Ranjbar P.Kashani AO. Eur. J. Org. Chem. 2011, 2128 -
54a
Karpov AS.Merkul E.Rominger F.Müller TJJ. Angew. Chem. Int. Ed. 2005, 44: 6951 -
54b
Mohamed Ahmed MS.Kobayashi K.Mori A. Org. Lett. 2005, 7: 4487 - 55
Iizuka M.Kondo Y. Eur. J. Org. Chem. 2007, 5180 - 56
Stonehouse JP.Chekmarev DS.Ivanova NV.Lang S.Pairaudeau G.Smith N.Stocks MJ.Sviridov SI.Utkina LM. Synlett 2008, 100 - 57
Imbeaux M.Mestdagh H.Moughamir K.Rolando C. J. Chem. Soc., Chem. Commun. 1992, 1678 - 58
Yu C.-M.Hong Y.-T.Lee J.-H. J. Org. Chem. 2004, 69: 8506 - 59
Roberts B.Liptrot D.Alcaraz L.Luker T.Stocks MJ. Org. Lett. 2010, 12: 4280 - 60
Ren W.Yamane M. J. Org. Chem. 2010, 75: 3017 - 61
Ren W.Yamane M. J. Org. Chem. 2010, 75: 8410 - 62
Ren W.Emi A.Yamane M. Synthesis 2011, 2303
References
For a more detailed discussion on the reaction mechanism, see references 2c-f and the articles cited therein.