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Synthesis 2007(13): 1970-1978
DOI: 10.1055/s-2007-983729
DOI: 10.1055/s-2007-983729
PAPER
© Georg Thieme Verlag Stuttgart · New YorkThe Surfactant-Promoted Cross-Coupling Reactions of Arylboronic Acids with Carboxylic Anhydrides or Acyl Chlorides in Water
Further Information
Received
19 March 2007
Publication Date:
18 June 2007 (online)
Publication History
Publication Date:
18 June 2007 (online)
Abstract
The palladium(II) chloride catalyzed cross-coupling of arylboronic acids with carboxylic anhydrides or acyl chlorides in water in the presence of various surfactants is described. The inexpensive and industrially widely used sodium dodecyl sulfate (SDS) was found to be a good promoter of the coupling reaction and aryl ketones were obtained in good yields without the use of phosphine ligands. The reactions were unaffected by the presence of electron-releasing and electron-withdrawing substituents in both the arylboronic acids and carboxylic derivatives and a variety of aryl ketones were obtained under mild conditions in air.
Key words
aryl ketone - boronic acid - carboxylic anhydride - acyl chloride - palladium catalysis
- 1a
Dieter RK. Tetrahedron 1999, 55: 4177 - 1b
Zhang YD.Rovis T. J. Am. Chem. Soc. 2004, 126: 15964 - 1c
Hatano B.Kadokawa JI.Tagaya H. Tetrahedron Lett. 2002, 43: 5859 - 2a
Furstner A.Voigtlander D.Schrader W.Giebel D.Reetz MT. Org. Lett. 2001, 3: 417 - 2b
Gmouh S.Yang H.Vaultier M. Org. Lett. 2003, 5: 2219 - 2c
Fillion E.Fishlock D.Wilsily A.Goll JM. J. Org. Chem. 2005, 70: 1316 - 3
Ross J.Xiao JL. Green Chem. 2002, 4: 129 - 4
Labadie JW.Stille JK. J. Am. Chem. Soc. 1983, 105: 669 - 5a
Wang XJ.Zhang L.Sun X.Xu Y.Krishnamurthy D.Senanayake CH. Org. Lett. 2005, 7: 5593 - 5b
Wang DH.Zhang ZZ. Org. Lett. 2003, 5: 4645 - 6
Arisawa M.Torisawa Y.Kawahara M.Yamanaka M.Nishida A.Nakagawa M. J. Org. Chem. 1997, 62: 4327 - 7a
Eberle MK.Kahle GG. Tetrahedron Lett. 1980, 21: 2303 - 7b
Rubottom GM.Kim CW. J. Org. Chem. 1983, 48: 1550 - 8a
Gooßen LJ.Ghosh K. Chem. Commun. 2001, 2084 - 8b
Gooßen LJ.Winkel L.Döhring A.Ghosh K.Paetzold J. Synlett 2002, 1237 - 8c
Kakino R.Shimizu I.Yamamoto A. Bull. Chem. Soc. Jpn. 2001, 74: 371 - 9a
Han C.Min ZD. Org. Lett. 2000, 2: 1649 - 9b
Urawa Y.Ogura K. Tetrahedron Lett. 2003, 44: 271 - 9c
Wang JX.Wei BG.Hu YL.Liu ZX.Yang YH. Synth. Commun. 2001, 31: 3885 - 9d
Bandgar BP.Patil AV. Tetrahedron Lett. 2005, 46: 7627 - 9e
Eddarir S.Cotelle N.Bakkour Y.Rolando C. Tetrahedron Lett. 2003, 44: 5359 - 10
Tatamidani H.Kakiuchi F.Chatani N. Org. Lett. 2004, 6: 3597 - 11a
Liebeskind LS.Srogl J. J. Am. Chem. Soc. 2000, 122: 11260 - 11b
Yu Y.Liebeskind LS. J. Org. Chem. 2004, 69: 3554 - 12
Zapf A. Angew. Chem. Int. Ed. 2003, 42: 5394 - 13a
Miyaura N.Suzuki A. Chem. Rev. 1995, 95: 2457 - 13b
Littke AF.Fu GC. Angew. Chem. Int. Ed. 2002, 41: 4176 - 13c
Hassan J.Sevignon M.Gozzi C.Schulz E.Lemaire M. Chem. Rev. 2002, 102: 1359 - 13d
Suzuki A. J. Organomet. Chem. 2002, 653: 83 - 14a
Bumagin NA.Korolev DN. Tetrahedron Lett. 1999, 40: 3057 - 14b
Haddach M.McCarthy JR. Tetrahedron Lett. 1999, 40: 3109 - 14c
Lysen M.Kelleher S.Begtrup M.Kristensen JL. J. Org. Chem. 2005, 70: 5342 - 14d
Kabalka GW.Malladi RR.Tejedor D.Kelley S. Tetrahedron Lett. 2000, 41: 999 - 15a
Kakino R.Narahashi H.Shimizu I.Yamamoto A. Chem. Lett. 2001, 1242 - 15b
Gooßen LJ.Ghosh K. Angew. Chem. Int. Ed. 2001, 40: 3458 - 16a
Genet JP.Savignac M. J. Organomet. Chem. 1999, 576: 305 - 16b
Leadbeater NE.Marco M. Org. Lett. 2002, 4: 2973 - 17a
Li CJ. Chem. Rev. 2005, 105: 3095 - 17b
Lindström UM. Chem. Rev. 2002, 102: 2751 - 18
Carrettin S.Guzman J.Corma A. Angew. Chem. Int. Ed. 2005, 44: 2242 - 19
Xin BW.Zhang YH.Cheng K. J. Org. Chem. 2006, 71: 5725 - 20a
Dwars T.Paetzold E.Oehme G. Angew. Chem. Int. Ed. 2005, 44: 7174 - 20b
Bunton CA.Nome F.Quina FH.Romsted LS. Acc. Chem. Res. 1991, 24: 357 - 21
Riisager A.Hanson BE. J. Mol. Catal. A: Chem. 2002, 189: 195 - 22a
Paetzold E.Jovel I.Oehme G. J. Mol. Catal. A: Chem. 2004, 214: 241 - 22b
Bhattacharya S.Srivastava A.Sengupta S. Tetrahedron Lett. 2005, 46: 3557 - 22c
Tascioglu S. Tetrahedron 1996, 52: 11113 - 23
Leadbeater NE. Chem. Commun. 2005, 2881 - 24
Beletskaya IP. Pure Appl. Chem. 1997, 69: 471 - 25
Cheprakov AV.Ponomareva NV.Beletskaya IP. J. Organomet. Chem. 1995, 486: 297 - 26a
Arcadi A.Cerichelli G.Chiarini M.Correa M.Zorzan D. Eur. J. Org. Chem. 2003, 4080 - 26b
Paetzold E.Oehme G. J. Mol. Catal. A: Chem. 2000, 152: 69 - 27
Kakino R.Narahashi H.Shimizu I.Yamamoto A. Bull. Chem. Soc. Jpn. 2002, 75: 1333 - 28
Kakino R.Yasumi S.Shimizu I.Yamamoto A. Bull. Chem. Soc. Jpn. 2002, 75: 137 - 29
Gooßen LJ.Ghosh K. Eur. J. Org. Chem. 2002, 3254 - 30
Oehme G.Grassert I.Paetzold E.Meisel R.Drexler K.Fuhrmann H. Coord. Chem. Rev. 1999, 185: 585 - 31
Rieke RD.Kim SH.Wu X. J. Org. Chem. 1997, 62: 6921 - 32
Christophe D.Filip B.Ioannis S.Tobias JK.Gérard C.Paul K. Angew. Chem. Int. Ed. 2004, 43: 2968 - 33
Taylor HM.Jones CD.Davenport JD.Hirsch KS.Kress TJ.Weaver D. J. Med. Chem. 1987, 30: 1359 - 34
James HPU.Gregor GR. Tetrahedron 2002, 58: 5251 - 35
Sarvari MH.Sharghi H. Synthesis 2004, 2165 - 36
Goethals G.Doucet JP.Bauer P.Uzan R. Spectrochim. Acta, Part A 1975, 31: 1501 - 37
Sapountzis I.Lin W.Kofink CC.Despotopoulou C.Knochel P. Angew. Chem. Int. Ed. 2005, 44: 1654 - 38
Mona HS.Hashem S. J. Org. Chem. 2004, 69: 6953 - 39
Merritt B.Andrus YM.Yunfu Z.Chun S. Tetrahedron Lett. 2002, 43: 9137MissingFormLabel - 40
Krug C.Hartwig JF. J. Am. Chem. Soc. 2002, 124: 1674 - 41
Kegelman MR.Brown EV. J. Am. Chem. Soc. 1954, 76: 2711 - 42
Kang SK.Ryu HC.Lee SW. Synth. Commun. 2001, 31: 1027 - 43
Lucjan S.Roman LW.Marek TC.Agnieszka C.Steven P. J. Org. Chem. 1989, 54: 6120 - 44
Tatamidani H.Yokota K.Kakiuchi F.Chatani N. J. Org. Chem. 2004, 69: 5615