Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Download PDF
Synthesis 2006(5): 860-864
DOI: 10.1055/s-2006-926323
DOI: 10.1055/s-2006-926323
PAPER
© Georg Thieme Verlag Stuttgart · New YorkReusable and Efficient Pd(OAc)2/TBAB/PEG-400 System for Suzuki-Miyaura Cross-Coupling Reaction under Ligand-Free Conditions
Further Information
Received
18 August 2005
Publication Date:
07 February 2006 (online)
Publication History
Publication Date:
07 February 2006 (online)
Abstract
The combination of Pd(OAc)2, TBAB and PEG-400 [poly(ethylene glycol-400)] was introduced as a reusable and efficient system for the Suzuki-Miyaura cross-coupling reaction. In the presence of 0.01 to 3 mol% of Pd(OAc)2, 10 mol% of TBAB, 2 equivalents of K2CO3 and 4 g of PEG-400, a number of aryl halides were coupled with arylboronic acids efficiently to afford moderate to excellent yields of the corresponding products under ligand-free conditions. Moreover, the system can be reused three times without any loss of catalytic activity.
Key words
Pd(OAc)2 - TBAB - PEG-400 - Suzuki-Miyaura cross-coupling reaction - aryl halides - arylboronic acids
- 1a
Bringmann G.Walter R.Weirich R. Angew. Chem., Int. Ed. Engl. 1990, 29: 977 - 1b
Hegedus LS. In Organometallics in SynthesisSchlosser M. Wiley; Chichester: 2002. p.1123 - 1c
Handbook of Organopalladium Chemistry for Organic Synthesis
Negishi E. Wiley-Interscience; New York: 2002. - For reviews, see:
- 2a
Miyaura N.Suzuki A. Chem. Rev. 1995, 95: 2457 - 2b
Diederich F.Stang PJ. Metal-Catalyzed Cross-Coupling Reactions Wiley-VCH; Weinheim: 1998. - 2c
Miyaura N. Cross-Coupling Reaction Springer; Berlin: 2002. - 2d
Nakamura I.Yamamoto Y. Chem. Rev. 2004, 104: 2127 - 2e
Bellina F.Carpita A.Rossi R. Synthesis 2004, 2419 - For selected papers on phosphine-palladium catalysts, see:
- 3a
Kwong FY.Lam WH.Yeung CH.Chan KS.Chan ASC. Chem. Commun. 2004, 2336 - 3b
Brenstrum T.Gerristma DA.Adjabeng GM.Frampton CS.Britten J.Robertson AJ.McNulty J.Capretta A. J. Org. Chem. 2004, 69: 77635 - 3c
Baillie C.Zhang L.Xiao J. J. Org. Chem. 2004, 69: 7779 - 3d
DeVasher RB.Moore LR.Shaughnessy KH. J. Org. Chem. 2004, 69: 7919 - 3e
Mukherjee A.Sarkar A. Tetrahedron Lett. 2004, 45: 9525 - 3f
Zhang W.Shi M. Tetrahedron Lett. 2004, 45: 8921 - 3g
Peyroux E.Berthiol F.Doucet H.Santelli M. Eur. J. Org. Chem. 2004, 1075 - 3h
Willis MC.Powell LH.Claverie CK. Angew. Chem. Int. Ed. 2004, 43: 1249 - 3i
Wang A.-E.Zhang J.Xie J.-H.Li K.Zhou Q.-L. Adv. Synth. Catal. 2004, 346: 595 - 3j
Berthiol F.Kondolff I.Doucet H.Santelli M. J. Organomet. Chem. 2004, 689: 2786 - 3k
Okamoto K.Akiyama R.Kobayashi S. Org. Lett. 2004, 6: 1987 - 3l
Barder TE.Buchwald SL. Org. Lett. 2004, 6: 2649 - 3m
Colacot TJ.Shea HA. Org. Lett. 2004, 6: 3731 - 3n
Barder TE.Walker SD.Martinelli JR.Buchwald SL. J. Am. Chem. Soc. 2005, 127: 4685 - For recent reviews on N-heterocyclic carbene-palladium catalysts, see:
- 4a
Herrmann WA. Angew. Chem. Int. Ed. 2002, 41: 1290 - 4b
Yong BS.Nolan SP. Chemtracts: Org. Chem. 2003, 205 - 5 For a paper on thiourea-palladium catalysts, see:
Dai M.Liang B.Wang C.Chen J.Yang Z. Org. Lett. 2004, 6: 221 - For representative papers on diazabutadiene-palladium catalysts, see:
- 6a
Grasa GA.Hillier AC.Nolan SP. Org. Lett. 2001, 3: 1077 - 6b
Palencia H.Garcia-Jimenez F.Takacs JM. Tetrahedron Lett. 2004, 45: 3849 - 6c
Mino T.Shirae Y.Sakamoto M.Fujita T. J. Org. Chem. 2005, 70: 2191 - For representative papers on amine-palladium catalysts, see:
- 7a
Tao B.Boykin DW. Tetrahedron Lett. 2003, 43: 7993 - 7b
Tao B.Boykin DW. J. Org. Chem. 2004, 69: 4330 - 7c
Li J.-H.Liu W.-J. Org. Lett. 2004, 6: 2809 - 7d
Li J.-H.Liu W.-J.Xie Y.-X. J. Org. Chem. 2005, 70: 5409 - 7e
Li J.-H.Zhang X.-D.Xie Y.-X. Synlett 2005, 1897 - For selected papers on other phosphine-free-ligand palladium catalysts, see:
- 8a
Gupta AK.Rim CY.Oh CH. Synlett 2004, 2227 - 8b
Fairlamb IJS.Kapdi AR.Lee AF. Org. Lett. 2004, 6: 4435 - 8c
Bandgar BP.Bettigeri SV.Phopase J. Tetrahedron Lett. 2004, 45: 6959 - 8d
Blanco B.Mehdi A.Moreno-Mañas M.Pleixats R.Reyé C. Tetrahedron Lett. 2004, 45: 8789 - 8e
Altenholf G.G oddard R.Lehmann CW.Glorius F. J. Am. Chem. Soc. 2004, 126: 15195 - For selected papers on PEG as a medium, see:
- 9a
Santaniello E.Manzocchi A.Sozzani P. Tetrahedron Lett. 1979, 20: 4581 - 9b
Santaniello E.Fiecchi A.Manzocchi A.Ferraboschi P. J. Org. Chem. 1983, 48: 3074 - 9c
Chandrasekar S.Narsihmulu Ch.Sultana SS.Reddy NRK. Org. Lett. 2002, 4: 4399 - 9d
Chandrasekar S.Narsihmulu Ch.Sultana SS.Reddy NRK. Chem. Commun. 2002, 1716 - 9e
Chandrasekar S.Narsihmulu Ch.Saritha B.Sultana SS. Tetrahedron Lett. 2004, 45: 5865 ; and references cited therein - 9f
Li J.-H.Zhu Q.-M.Liang Y.Yang D. J. Org. Chem. 2005, 70: 5347 - 9g
Namboodiri VV.Varma RS. Green Chem. 2001, 3: 146 - For some representative papers on TBAB-promoted palladium-catalyzed Suzuki-Miyaura cross-coupling reactions, see:
- 10a
Badone D.Baroni M Cardamone R.Ielmini A.Guzzi U. J. Org. Chem. 1997, 62: 7170 - 10b
Bedford RB.Blake ME.Butts CP.Holder D. Chem. Commun. 2003, 466 - 10c
Lysén M.Köhler K. Synlett 2005, 1671 ; and references cited therein - 10d
Arvela RK.Leadbeater NE. Org. Lett. 2005, 7: 2101 - 10e
Reetz MT.Breinbauer R.Wanninger K. Tetrahedron Lett. 1996, 37: 4499 - 10f
Reetz MT.de Vries JG. Chem. Commun. 2004, 1559 ; and references cited therein