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Synthesis 2010(18): 3163-3173
DOI: 10.1055/s-0030-1258181
DOI: 10.1055/s-0030-1258181
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkFacile Access to Biaryls and 2-Acetyl-5-arylbenzofurans via Suzuki Coupling in Water under Thermal and Microwave Conditions
Further Information
Received
12 March 2010
Publication Date:
16 July 2010 (online)
Publication History
Publication Date:
16 July 2010 (online)
Abstract
The phosphine-free Suzuki-Miyaura carbon-carbon cross-coupling reactions of activated and deactivated aryl halides and 2-acetyl-5-bromobenzofuran with various aryl- or heteroarylboronic acids were investigated. A benzothiazole-based palladium(II) complex was used as a precatalyst for the reactions under both thermal and microwave conditions in air using water as a solvent.
Key words
palladium - catalysis - microwave irradiation - Suzuki reactions - benzofuran
- 1a
Hassan J.Sevignon M.Gozzi C.Schulz E.Lemaire M. Chem. Rev. 2002, 102: 1359Reference Ris Wihthout Link - 1b
Corbet J.-P.Mignani G. Chem. Rev. 2006, 106: 2651Reference Ris Wihthout Link - 1c
Yin L.Liebscher J. Chem. Rev. 2007, 107: 133Reference Ris Wihthout Link - 1d
Alberico D.Scott ME.Lautens M. Chem. Rev. 2007, 107: 174Reference Ris Wihthout Link - 1e
Catellani M.Motti E.Della Ca’ N.Ferraccioli R. Eur. J. Org. Chem. 2007, 4153Reference Ris Wihthout Link - 1f
Bellina F.Rossi R. Tetrahedron 2009, 65: 10269Reference Ris Wihthout Link - 1g
Ackermann L.Vicente R.Kapdi AR. Angew. Chem. Int. Ed. 2009, 48: 9792Reference Ris Wihthout Link - 2
Handbook
of Organopalladium Chemistry for Organic Synthesis
Negishi E. Wiley-Interscience; Hoboken NJ: 2002. - 3a
Miyaura N.Suzuki A. Chem. Rev. 1995, 95: 2457Reference Ris Wihthout Link - 3b
Bellina F.Carpita A.Rossi R. Synthesis 2004, 2419Reference Ris Wihthout Link - 3c
Hall D. G. In Boronic Acids Preparation, Applications in Organic Synthesis and MedicineHall DG. Wiley-VCH; Weinheim: 2005. p.1-99Reference Ris Wihthout Link - 3d
Molander GA.Canturk B. Angew. Chem. Int. Ed. 2009, 48: 9240Reference Ris Wihthout Link - 4
Kertesz M.Choi CH.Yang S. Chem. Rev. 2005, 105: 3448 - 5
Kaye S.Fox JM.Hicks FA.Buchwald SL. Adv. Synth. Catal. 2001, 343: 789 - 6
Kotha S.Lahiri K.Kashinath D. Tetrahedron 2002, 58: 9633 - 7
Microwaves in Organic Synthesis
Loupy A. Wiley-VCH; Weinheim: 2002. - 8a
Kappe CO. Angew. Chem. Int. Ed. 2004, 43: 6250Reference Ris Wihthout Link - 8b
Hoz A.Ortiz AD.Moreno A. Chem. Soc. Rev. 2005, 34: 164Reference Ris Wihthout Link - 9a
Dupont J.Consorti CS.Spencer J. Chem. Rev. 2005, 105: 2527Reference Ris Wihthout Link - 9b
Anderson KW.Buchwald SL. Angew. Chem. Int. Ed. 2005, 44: 6173Reference Ris Wihthout Link - 9c
Korolev DN.Bumagin NA. Tetrahedron Lett. 2005, 46: 5751Reference Ris Wihthout Link - 9d
Lysén M.Köhler K. Synlett 2005, 1671Reference Ris Wihthout Link - 10a
Wyatt PG.Allen MJ.Chilcott J.Gardner CJ.Livermore DG.Mordaunt MJE.Nerozzi F.Patel M.Perren MJ.Weingarten GG.Shabbir S.Woollard PM.Zhou P. Bioorg. Med. Chem. Lett. 2002, 12: 1405Reference Ris Wihthout Link - 10b
Smith RA.Chen J.Mader MM.Muegge I.Moehler U.Katti S.Marrero D.Stirtan WG.Weaver DR.Xiao H.Carley W. Bioorg. Med. Chem. Lett. 2002, 12: 2875Reference Ris Wihthout Link - 10c
Hayakawa I.Shioya R.Agatsuma T.Furukawa H.Sugano Y. Bioorg. Med. Chem. Lett. 2004, 14: 3411Reference Ris Wihthout Link - 10d
Cowart M.Faghih R.Curtis MP.Gfesser GA.Bennani YL.Black LA.Pan L.Marsh KC.Sullivan JP.Esbenshade TA.Fox GB.Hancock AA. J. Med. Chem. 2005, 48: 38Reference Ris Wihthout Link - 11a
Halabalaki M.Aligiannis N.Papoutsi Z.Mitakou S.Moutsatsou P.Sekeris C.Skaltsounis A. J. Nat. Prod. 2000, 63: 1672Reference Ris Wihthout Link - 11b
Apers S.Paper D.Bürgermeister J.Baronikova S.Van Dyck S.Lemière G.Vlietinck A.Pieters L. J. Nat. Prod. 2002, 65: 718Reference Ris Wihthout Link - 11c
Stevenson PC.Simmonds MSJ.Yule MA.Veitch NC.Kite GC.Irwin D.Legg M. Phytochemistry 2003, 63: 41Reference Ris Wihthout Link - 11d
Ali Z.Tanaka T.Iliya I.Iinuma M.Furusawa M.Ito T.Nakaya K.-i.Murata J.Darnaedi D. J. Nat. Prod. 2003, 66: 558Reference Ris Wihthout Link - 11e
Kokialakis N.Magiatis P.Mitaku S.Pratsinis H.Tillequin F. Planta Med. 2003, 69: 566Reference Ris Wihthout Link - 12a
Aslam SN.Stevenson PC.Phythian SJ.Veitch NC.Hall DR. Tetrahedron 2006, 62: 4214Reference Ris Wihthout Link - 12b
Ober AG.Fronczek FR.Fischer NH. J. Nat. Prod. 1985, 48: 242Reference Ris Wihthout Link - 13a
Abdel-Aziz HA.Mekawey AAI.Dawood KM. Eur. J. Med. Chem. 2009, 44: 3637Reference Ris Wihthout Link - 13b
Dawood KM.Abdel-Gawad H.Rageb EA.Ellithey M.Mohamed HA. Bioorg. Med. Chem. 2006, 14: 3672Reference Ris Wihthout Link - 13c
Farag AM.Dawood KM.Abdelaziz HA. J. Chem. Res. 2005, 378Reference Ris Wihthout Link - 14a
Dawood KM.Fuchigami T. Synlett 2003, 1631Reference Ris Wihthout Link - 14b
Dawood KM.Fuchigami T. J. Org. Chem. 2004, 69: 5302Reference Ris Wihthout Link - 15a
Dawood KM.Kirschning A. Tetrahedron 2005, 61: 12121Reference Ris Wihthout Link - 15b
Dawood KM. Tetrahedron 2007, 63: 9642Reference Ris Wihthout Link - 15c
Dawood KM.Eldeftar MM. Synthesis 2010, 1030Reference Ris Wihthout Link - 15d
Dawood KM.Fayed MS.Elkhalea MM. ARKIVOC 2009, (xiii): 324Reference Ris Wihthout Link - 16a
Solodenko W.Brochwitz C.Wartchow R.Hashem MdA.Vaultier M.Dawood KM.Kirschning A. Mol. Diversity 2005, 9: 333Reference Ris Wihthout Link - 16b
Dawood KM.Solodenko W.Kirschning A. ARKIVOC 2007, (v): 104Reference Ris Wihthout Link - 17
Bushey DF.Johnson BF.Huang J. J. Org. Chem. 1985, 50: 2091 - 18
Farina V. Adv. Synth. Catal. 2004, 346: 1553 - 19a
Nowotny M.Hanefeld U.van Koningsveld H.Maschmeyer T. Chem. Commun. 2000, 1877Reference Ris Wihthout Link - 19b
Yu K.Sommer W.Richardson JM.Weck M.Jones CW. Adv. Synth. Catal. 2005, 347: 161Reference Ris Wihthout Link - 19c
Bergbreiter DE.Osburn PL.Frels JD. Adv. Synth. Catal. 2005, 347: 172Reference Ris Wihthout Link - 20a
Carey JS.Laffan D.Thomson C.Williams MT. Org. Biomol. Chem. 2006, 4: 2337Reference Ris Wihthout Link - 20b
Bonnet V.Mongin F.Tricourt F.Breton G.Marsais F.Knochel P.Quaquiner G. Synlett 2002, 1008Reference Ris Wihthout Link - 21
Friesen RW.Brideau C.Chan CC.Charleson S.Deschênes D.Dube D.Ethier D.Fortin R.Gauthier JY.Girard Y.Gordon R.Greig GM.Riendeau D.Savoie C.Wang Z.Wong E.Visco D.Xu LJ.Young RN. Bioorg. Med. Chem. Lett. 1998, 8: 2777 - 22
Quirk J.Thornton M.Kirkpatrick P. Nature (London) 2003, 2: 769 - 23
Capdeville R.Buchdunger E.Zimmermann J.Matter A. Nature (London) 2002, 1: 493 - 24a
Bedford RB.Cazin CSJ.Holder D. Coord. Chem. Rev. 2004, 248: 2283Reference Ris Wihthout Link - 24b
Littke AF.Fu GC. Angew. Chem. Int. Ed. 2002, 41: 4176Reference Ris Wihthout Link - 24c
Herrmann WA.Bohm VPW.Reisinger CP. J. Organomet. Chem. 1999, 576: 23Reference Ris Wihthout Link - 25
Child RG,Wilkinson RG, andTomcufcik AS. inventors; US 3931157. ; Chem. Abstr. 1976, 84, 12915Reference Ris Wihthout Link - 26
Chen Y.-Z. Mikrochimica Acta 1981, 75: 343 - 27
Yang J. J. Org. Chem. 1999, 64: 9251 - 28
Paizs C. Tetrahedron: Asymmetry 2003, 14: 1495 - 29
Zhu L.Duquette J.Zhang M. J. Org. Chem. 2003, 68: 3729 - 30a
Desmarets C. Tetrahedron 2008, 64: 372Reference Ris Wihthout Link - 30b
You E. Synthesis 2006, 1465Reference Ris Wihthout Link - 31
Zhang G. J. Chem. Res. 2004, 9: 593 - 32
Brewster CM. J. Am. Chem. Soc. 1939, 61: 3083 - 33
Minabe M. J. Org. Chem. 1987, 52: 1745 - 34
Qin Y. Synlett 2007, 2410 - 35
Huber WF. J. Am. Chem. Soc. 1946, 68: 1109 - 36
Wallow TL.Novak BM. J. Org. Chem. 1994, 59: 5034 - 37
Gull HC. J. Chem. Soc. 1929, 491 - 38
Shelby NQ.Stambuli JP.Hartwig JF. J. Org. Chem. 2002, 67: 5553 - 39a
Sapountzis I. Angew. Chem. Int. Ed. 2005, 44: 1654Reference Ris Wihthout Link - 39b
Rao MLN. Tetrahedron 2008, 64: 5762Reference Ris Wihthout Link - 40
Francis HC.Thomas JK. J. Am. Chem. Soc. 1956, 78: 5842 - 41
Daab JC. Monatsh. Chem. 2003, 134: 573 - 42
Coleman GH. inventors; US 2196576.Reference Ris Wihthout Link