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Synthesis 2007(7): 984-988
DOI: 10.1055/s-2007-965958
DOI: 10.1055/s-2007-965958
PAPER
© Georg Thieme Verlag Stuttgart · New York
TBAB-Promoted Ligand-Free Copper-Catalyzed Cross-Coupling Reactions of Aryl Halides with Arylboronic Acids
Weitere Informationen
Received
5 December 2006
Publikationsdatum:
28. Februar 2007 (online)
Publikationsverlauf
Publikationsdatum:
28. Februar 2007 (online)
Abstract
Tetrabutylammonium bromide (TBAB) was found to improve the ligand-free copper-catalyzed cross-couplings of aryl halides with arylboronic acids. In the presence of 10 mol% of CuI and 20 mol% of TBAB, a variety of aryl halides underwent the coupling with arylboronic acids smoothly to afford the corresponding products in moderate to good yields.
Key words
tetrabutylammonium bromide - copper(I) iodide - aryl halide - arylboronic acid - Suzuki-Miyaura cross-coupling reaction
- For reviews, see:
-
1a
Bringmann G.Walter R.Weirich R. Angew. Chem., Int. Ed. Engl. 1990, 29: 977 -
1b
Miyaura N.Suzuki A. Chem. Rev. 1995, 95: 2457 -
1c
Diederich F.Stang PJ. Metal-Catalyzed Cross-Coupling Reactions Wiley-VCH; Weinheim: 1998. -
1d
Miyaura N. Cross-Coupling Reaction Springer; Berlin: 2002. -
1e
Negishi E. Handbook of Organopalladium Chemistry for Organic Synthesis Wiley-Interscience; New York: 2002. -
1f
Yong BS.Nolan SP. Chemtracts: Org. Chem. 2003, 205 -
1g
Tang S.Liang Y.Liu W.-J.Li J.-H. Chin. J. Org. Chem. 2004, 24: 1133 ; Chem. Abstr. 2005, 142, 93160 -
1h
de Meijere A.Diederich F. Metal-Catalyzed Cross-Coupling Reactions Wiley-VCH; Weinheim: 2004. -
1i
Phan NTS.van der Sluys M.Jone CP. Adv. Synth. Catal. 2006, 348: 609 - For special reviews on copper-catalyzed cross-couplings, see:
-
2a
Siemsen P.Livingston RC.Diederich F. Angew. Chem. Int. Ed. 2000, 39: 2632 -
2b
Hassan J.Sevignon M.Gozzi C.Schulz E.Lemaire M. Chem. Rev. 2002, 102: 1359 -
2c
Ley SV.Thomas AW. Angew. Chem. Int. Ed. 2003, 42: 5400 -
2d
Beletskaya IP.Cheprakov AV. Coord. Chem. Rev. 2004, 248: 2337 - For representative papers on the nickel-catalyzed Suzuki-Miyaura cross-coupling reaction, see:
-
3a
Saito S.Ohtani S.Miyaura N. J. Org. Chem. 1997, 62: 8024 -
3b
Zim D.Lando VR.Dupond J.Monteiro AL. Org. Lett. 2001, 3: 3049 -
3c
Percec V.Golding GM.Smidrkal J.Weichold O. J. Org. Chem. 2004, 69: 3447 - For papers on the copper-catalyzed Suzuki-Miyaura cross-coupling reaction, see:
-
4a
Thathagar MB.Beckers J.Rothenberg G. J. Am. Chem. Soc. 2002, 124: 11858 -
4b
Thathagar MB.Beckers J.Rothenberg G. Adv. Synth. Catal. 2003, 345: 979 -
4c
Li J.-H.Li J.-L.Wang D.-P.Pi S.-F.Xie Y.-X.Zhang M.-B.Hu X.-C. J. Org. Chem. 2007, 72: in press (DOI: 10.1021/jo0623742) - For papers on the other cross-coupling reaction catalyzed by a catalytic amount of copper, see: (Sonogashira reaction)
-
5a
Okuro K.Furuune M.Enna M.Miura M.Nomura M. J. Org. Chem. 1993, 58: 4716 -
5b
Gujadhur RK.Bates CG.Venkataraman D. Org. Lett. 2001, 3: 4315 -
5c
Thathagar MB.Beckers J.Rothenberg G. Green Chem. 2004, 6: 215 -
5d
Ma D.Liu F. Chem. Commun. 2004, 1934 -
5e
Wang YF.Deng W.Liu L.Guo QX. Chin. Chem. Lett. 2005, 16: 1197 ; Chem. Abstr. 2005, 144, 22662 -
5f
Saejueng P.Bates CG.Venkataraman D. Synthesis 2005, 1706 -
5g
Xie Y.-X.Deng C.-L.Pi S.-F.Li J.-H.Yin D.-L. Chin. J. Chem. 2006, 24: 1290 - (Stille reaction)
-
5h
Kang S.-K.Kim J.-S.Choi S.-C. J. Org. Chem. 1997, 62: 4208 -
5i
Wang Y.Burton DJ. Org. Lett. 2006, 8: 1109 -
5j
Mohapatra S.Bandyopadhyay A.Barma DK.Capdevila JH.Falck JR. Org. Lett. 2003, 5: 4759 -
5k
Kang S.-K.Yamaguchi T.Kim T.-H.Ho P.-S. J. Org. Chem. 1996, 61: 9082 -
5l
Li J.-H.Tang B.-X.Tao L.-M.Liang Y.Zhang M.-B. J. Org. Chem. 2006, 71: 7488 - 6 For a paper on the use of the CuI/DABCO catalytic system for Heck reaction, see:
Li J.-H.Wang D.-P.Xie Y.-X. Tetrahedron Lett. 2005, 46: 4941 - 7 For a preliminary communication, see:
Li J.-H.Wang D.-P. Eur. J. Org. Chem. 2006, 2063 - 8
Stephens RD.Castro CE. J. Org. Chem. 1963, 28: 2163 - For the representative papers on TBAB-promoted palladium-catalyzed Suzuki-Miyaura cross-coupling reactions, see:
-
9a
Reetz MT.de Vries JG. Chem. Commun. 2004, 1559 ; and references cited therein -
9b
Liu W.-J.Xie Y.-X.Liang Y.Li J.-H. Synthesis 2006, 860 -
9c
Bedford RB.Blake ME.Butts CP.Holder D. Chem. Commun. 2003, 466 - 10
Venkatraman S.Li C.-J. Org. Lett. 1999, 1: 1133 - 11
Littke AF.Dai C.Fu GC. J. Am. Chem. Soc. 2000, 122: 4020 - 12
Pridgen LN.Jones SS. J. Org. Chem. 1982, 47: 1590 - 13
Wynberg H.van Driel H. J. Am. Chem. Soc. 1965, 87: 3998 - 14
Molander GA.Biolatto B. J. Org. Chem. 2003, 68: 4302 - 15
Akiyama R.Kobayashi S. Angew. Chem. Int. Ed. 2001, 40: 3469 - 16
Zeni G.Braga AL.Stefani HA. Acc. Chem. Res. 2003, 36: 731 ; and references cited therein