Abstract
A literature overview, up to the end of 2004, of the most important microwave-assisted transition-metal-mediated processes used for the decoration and construction of heterocycles is presented. The emphasis of the chapter lies in the use of palladium-assisted reactions but examples of copper- and nickel-mediated processes are also incorporated.
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Abbreviations
- BARF:
-
tetra[3,5-bis(trifluoromethyl)phenyl]borate
- BINAP:
-
2,2′-bis(diphenylphosphanyl)-1,1′-binaphthyl
- BOC:
-
t-butoxycarbonyl
- Cbz:
-
benzyloxycarbonyl
- DCE:
-
1,2-dichloroethane
- DCPAB:
-
2-(dicyclohexylphosphanyl)-2′-(N,N-dimethylamino)biphenyl
- DCPB:
-
2-(dicyclohexylphosphanyl)biphenyl
- DME:
-
1,2-dimethoxyethane
- DMF:
-
N,N-dimethylformamide
- dmphen:
-
2,9-dimethyl-1,10-phenanthroline
- DMSO:
-
dimethyl sulfoxide
- dppf:
-
1,1′-bis(diphenylphosphanyl)ferrocene
- DTPB:
-
2-(di-t-butylphosphanyl)biphenyl
- NIS:
-
N-iodosuccinimide
- NMM:
-
N-methylmorpholine
- NMP:
-
N-methylpyrrolidinone
- Ms:
-
methanesulfonyl or mesyl
- phen:
-
1,10-phenanthroline
- PPFA:
-
N,N-dimethyl-1-[2-(diphenylphosphanyl)ferrocenyl]ethylamine
- SPE:
-
solid-phase extraction
- SPOS:
-
solid-phase organic synthesis
- TBAB:
-
tetrabutylammonium bromide
- TBDPS:
-
t-butyldiphenylsilyl
- TFA:
-
trifluoroacetic acid
- THF:
-
tetrahydrofuran
References
Muci AR, Buchwald SL (2002) Top Curr Chem 219:131
Littke AF, Fu GC (2002) Angew Chem, Int Ed 41:4176
Prim D, Campagne J-M, Joseph D, Andrioletti B (2002) Tetrahedron 58:2041
Kotha S, Lahiri K, Kashinath D (2002) Tetrahedron 58:9633
Beletskaya IP, Cheprakov AV (2000) Chem Rev 100:3009
Ley SV, Thomas AW (2003) Angew Chem, Int Ed 42:5400
Mizoroki T, Mori K, Ozaki A (1971) Bull Chem Soc Jpn 44:581
Heck RF, Nolley JP (1972) J Org Chem 37:2320
Sonogashira K, Tohda Y, Hagihara N (1975) Tetrahedron Lett 16:4467
Miyaura N, Suzuki A (1995) Chem Rev 95:2457
Milstein D, Stille JK (1978) J Am Chem Soc 100:3636
Milstein D, Stille JK (1979) J Am Chem Soc 101:4992
Guram AS, Rennels RA, Buchwald SL (1995) Angew Chem Int Ed 34:1348
Louie J, Hartwig JF (1995) Tetrahedron Lett 36:3609
Hayes BL (2002) Microwave synthesis: chemistry at the speed of light. CEM Publishing, Matthews
Loupy A (ed) (2002) Microwaves in organic synthesis. Wiley, New York
Hayes BL (2004) Aldrichim Acta 37:66
Lindström P, Tierney JP (eds) (2005) Microwave-assisted organic synthesis. Blackwell, Oxford
Kappe CO (2004) Angew Chem, Int Ed 43:6250
Stanetty P, Schnürch M, Mihovilovic MD (2003) Synlett 12:1862
Walla P, Kappe CO (2004) Chem Commun 5:564
Krascsenicsová K, Walla P, Kasák P, Uray G, Kappe CO, Putala M (2004) Chem Commun 22:2606
Mutule I, Suna E (2004) Tetrahedron Lett 45:3909
Bentz E, Moloney MG, Westaway SM (2004) Tetrahedron Lett 45:7395
Samuelsson L, Långström B (2003) J Label Compd Radiopharm 46:263
Rashatasakhon P, Ozdemir AD, Willis J, Padwa A (2004) Org Lett 6:917
Kaval N, Bisztray K, Dehaen W, Kappe CO, Van der Eycken E (2003) Mol Divers 7:125
Larhed M, Hoshino M, Hadida S, Curran DP, Hallberg A (1997) J Org Chem 62:5583
Alterman M, Andersson HO, Garg N, Ahlsén G, Lövgren S, Classon B, Danielson UH, Kvarnström I, Vrang L, Unge T, Samuelsson B, Hallberg A (1999) J Med Chem 42:3835
Zhang Y, Pavlova OA, Chefer SI, Hall AW, Kurian V, Brown LL, Kimes AS, Mukhin AG, Horti AG (2004) J Med Chem 47:2453
O'Neill DJ, Shen L, Prouty C, Conway BR, Westover L, Xu JZ, Zhang H-C, Maryanoff BE, Murray WV, Demarest KT, Kuo G-H (2004) Bioorg Med Chem 12:3167
Nehls BS, Asawapirom U, Füldner S, Preis E, Farrell T, Scherf U (2004) Adv Funct Mater 14:352
Berthault A, Berteina-Raboin S, Finaru A, Guillaumet G (2004) QSAR Comb Sci 23:850
Fînaru A, Berthault A, Besson T, Guillaumet G, Berteina-Raboin S (2002) Org Lett 4:2613
Larhed M, Lindeberg G, Hallberg A (1996) Tetrahedron Lett 37:8219
Blettner CG, König WA, Stenzel W, Schotten T (1999) J Org Chem 64:3885
Schaal W, Karlsson A, Ahlsén G, Lindberg J, Andersson HO, Danielson UH, Classon B, Unge T, Samuelsson B, Hultén J, Hallberg A, Karlén A (2001) J Med Chem 44:155
Villemin D, Caillot F (2001) Tetrahedron Lett 42:639
Villemin D, Gómez-Escalonilla MJ, Saint-Clair J-F (2001) Tetrahedron Lett 42:635
Öhberg L, Westman J (2001) Synlett 12:1893
Wilson NS, Sarko CR, Roth GP (2004) Org Process Res Dev 8:535
Melucci M, Barbarella G, Sotgiu G (2002) J Org Chem 67:8877
Melucci M, Barbarella G, Zambianchi M, Di Pietro P, Bongini A (2004) J Org Chem 69:4821
Sotgiu G, Zambianchi M, Barbarella G, Botta C (2002) Tetrahedron 58:2245
Luo G, Chen L, Poindexter GS (2002) Tetrahedron Lett 43:5739
Gong Y, He W (2002) Org Lett 4:3803
Fürstner A, Seidel G (2002) Org Lett 4:541
Appukkuttan P, Van der Eycken E, Dehaen W (2003) Synlett 8:1204
Leadbeater NE, Marco M (2002) Org Lett 4:2973
Bryson TA, Gibson JM, Stewart JJ, Voegtle H, Tiwari A, Dawson JH, Marley W, Harmon B (2003) Green Chem 5:177
Leadbeater NE, Marco M (2003) Angew Chem, Int Ed 42:1407
Leadbeater NE, Marco M (2003) J Org Chem 68:5660
Arvela RK, Leadbeater NE, Sangi MS, Williams VA, Granados P, Singer RD (2005) J Org Chem 70:161
Wang Y, Sauer DR (2004) Org Lett 6:2793
Wu TYH, Schultz PG, Ding S (2003) Org Lett 5:3587
Gong Y, He W (2004) Heterocycles 62:851
Nöteberg D, Schaal W, Hamelink E, Vrang L, Larhed M (2003) J Comb Chem 5:456
Ersmark K, Feierberg I, Bjelic S, Hamelink E, Hackett F, Blackman MJ, Hultén J, Samuelsson B, Åqvist J, Hallberg A (2004) J Med Chem 47:110
Organ MG, Mayer S, Lepifre F, N'Zemba B, Khatri J (2003) Mol Divers 7:211
Appukkuttan P, Orts AB, Chandran RP, Goeman JL, Van der Eycken J, Dehaen W, Van der Eycken E (2004) Eur J Org Chem 15:3277
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 (2004) J Med Chem 47:5995
Holmberg P, Sohn D, Leideborg R, Caldirola P, Zlatoidsky P, Hanson S, Mohell N, Rosqvist S, Nordvall G, Johansson AM, Johansson R (2004) J Med Chem 47:3927
Kurukulasuriya R, Sorensen BK, Link JT, Patel JR, Jae H-S, Winn MX, Rohde JR, Grihalde ND, Lin CW, Ogiela CA, Adler AL, Collins CA (2004) Bioorg Med Chem Lett 14:2047
Mont N, Fernández-Megido L, Teixidó J, Kappe CO, Borrell JI (2004) QSAR Comb Sci 23:836
Lu Y, Zhang W (2004) QSAR Comb Sci 23:827
Zhang W, Hiu-Tung Chen C, Lu Y, Nagashima T (2004) Org Lett 6:1473
Han JW, Castro JC, Burgess K (2003) Tetrahedron Lett 44:9359
Erdélyi M, Gogoll A (2001) J Org Chem 66:4165
Appukkuttan P, Dehaen W, Van der Eycken E (2003) Eur J Org Chem 4713
Leadbeater NE, Marco M, Tominack BJ (2003) Org Lett 5:2003
He H, Wu Y-J (2004) Tetrahedron Lett 45:3237
Qvortrup K, Andersson AS, Mayer J-P, Jepsen AS, Nielsen MB (2004) Synlett 2818
Petricci E, Radi M, Corelli F, Botta M (2003) Tetrahedron Lett 44:9181
Hopkins CR, Collar N (2004) Tetrahedron Lett 45:8631
Zhu J, Germain AR, Porco JA (2004) Angew Chem Int Ed 43:1239
Kwan PH, MacLachlan MJ, Swager TM (2004) J Am Chem Soc 126:8638
Alterman M, Hallberg A (2000) J Org Chem 65:7984
Zhang A, Neumeyer JL (2003) Org Lett 5:201
Zhang A, Xiong W, Bidlack JM, Hilbert JE, Knapp BI, Wentland MP, Neumeyer JL (2004) J Med Chem 47:165
Srivastava RR, Collibee SE (2004) Tetrahedron Lett 45:8895
Arvela RK, Leadbeater NE (2003) J Org Chem 68:9122
Arvela RK, Leadbeater NE, Torenius HM, Tye H (2003) Org Biomol Chem 1:1119
Pemberton N, Åberg V, Almstedt H, Westermark A, Almqvist F (2004) J Org Chem 69:7830
Gopalsamy A, Lim K, Ciszewski G, Park K, Ellingboe JW, Bloom J, Insaf S, Upeslacis J, Mansour TS, Krishnamurthy G, Damarla M, Pyatski Y, Ho D, Howe AYM, Orlowski M, Feld B, O'Connell J (2004) J Med Chem 47:6603
Larhed M, Hallberg A (1996) J Org Chem 61:9582
Nilsson P, Gold H, Larhed M, Hallberg A (2002) Synthesis 11:1611
Loiseleur O, Meier P, Pfaltz A (1996) Angew Chem, Int Ed 35:200
Vallin KSA, Emilsson P, Larhed M, Hallberg A (2002) J Org Chem 67:6243
Datta GK, Vallin KSA, Larhed M (2003) Mol Divers 7:107
Svennebring A, Nilsson P, Larhed M (2004) J Org Chem 69:3345
Stadler A, von Schenck H, Vallin KSA, Larhed M, Hallberg A (2004) Adv Synth Catal 346:1773
Andappan MMS, Nilsson P, von Schenck H, Larhed M (2004) J Org Chem 69:5212
Gracias V, Moore JD, Djuric SW (2004) Tetrahedron Lett 45:417
Sørensen US, Pombo-Villar E (2004) Helv Chim Acta 87:82
Wan Y, Alterman M, Hallberg A (2002) Synthesis 11:1597
Antane S (2003) Synth Commun 33:2145
Wang T, Magnin DR, Hamann LG (2003) Org Lett 5:897
Ullrich T, Giraud F (2003) Tetrahedron Lett 44:4207
Maes BUW, Loones KTJ, Lemière GLF, Dommisse RA (2003) Synlett 1822
Maes BUW, Loones KTJ, Hostyn S, Diels G (2004) Tetrahedron 60:11559
McCarroll AJ, Sandham DA, Titcomb LR, de K Lewis AK, Cloke FGN, Davies BP, de Santana AP, Hiller W, Caddick S (2003) Mol Divers 7:115
Burton G, Cao P, Li G, Rivero R (2003) Org Lett 5:4373
Harmata M, Hong X, Ghosh SK (2004) Tetrahedron Lett 45:5233
Brain CT, Steer JT (2003) J Org Chem 68:6814
Lange JHM, Hofmeyer LJF, Hout FAS, Osnabrug SJM, Verveer PC, Kruse CG, Feenstra RW (2002) Tetrahedron Lett 43:1101
Wu Y-J, He H, L'Heureux A (2003) Tetrahedron Lett 44:4217
Lengar A, Kappe CO (2004) Org Lett 6:771
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Maes, B.U.W. Transition-Metal-Based Carbon–Carbon and Carbon–Heteroatom Bond Formation for the Synthesis and Decoration of Heterocycles. In: Van der Eycken, E., Kappe, C.O. (eds) Microwave-Assisted Synthesis of Heterocycles. Topics in Heterocyclic Chemistry, vol 1. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_002
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