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
Synthesis 2009(23): 4075-4081
DOI: 10.1055/s-0029-1217032
DOI: 10.1055/s-0029-1217032
FEATUREARTICLE
© Georg Thieme Verlag
Stuttgart ˙ New YorkPalladium-Catalyzed Cross-Coupling Reaction of AlArEt2(THF) with Aryl Bromides
Further Information
Received
30 July 2009
Publication Date:
12 October 2009 (online)
Publication History
Publication Date:
12 October 2009 (online)

Abstract
Efficient cross-coupling reactions of aryl bromides with AlArEt2(THF) (Ar = Ph, 4-MeC6H4, 4-MeOC6H4, 4-Me3SiC6H4, or 2-naphthyl) catalyzed by a catalytic system of 1 mol% Pd(OAc)2 and 2 mol% PCy3 furnish aryl-aryl coupling products. The system works well for a wide range of aryl bromides regardless of the electronic or steric nature of the substituent on the aryl bromides.
Key words
cross-coupling - palladium - aryl - aluminum - biaryl
- 1a
Bringmann G.Gunther C.Ochse M.Schupp O.Tasler S. Progress in the Chemistry of Organic Natural Products Vol. 82:Herz W.Falk H.Kirby GW.Moore RE. Springer; New York: 2001. p.1-293 - 1b
Noguchi H.Hojo K.Suginome M. J. Am. Chem. Soc. 2007, 129: 758 - 2a
Miyaura N.Suzuki A. Chem. Rev. 1995, 95: 2457 - 2b
Hassan J.Sevignon M.Gozzi C.Schulz E.Lemaire M. Chem. Rev. 2002, 102: 1359 - 2c
Miyaura N. Top. Curr. Chem. 2002, 219: 11 - 3a
Navarro O.Kelly RA.Nolan SP. J. Am. Chem. Soc. 2003, 125: 16194 - 3b
Moore LR.Shaughnessy KH. Org. Lett. 2004, 6: 225 - 3c
Dong C.-G.Hu Q.-S. J. Am. Chem. Soc. 2005, 127: 10006 - 3d
Barder TE.Walker SD.Martinelli JR.Buchwald SL. J. Am. Chem. Soc. 2005, 127: 4685 - 3e
González-Bobes F.Fu GC. J. Am. Chem. Soc. 2006, 128: 5360 - 3f
Imao D.Glasspoole BW.Laberge VS.Crudden CM. J. Am. Chem. Soc. 2009, 131: 5024 - 4a
Espinet P.Echavarren AM. Angew. Chem. Int. Ed. 2004, 43: 4704 - 4b
Su W.Urgaonkar S.McLaughlin PA.Verkade JG. J. Am. Chem. Soc. 2004, 126: 16433 - 4c
Powell DA.Maki T.Fu GC. J. Am. Chem. Soc. 2005, 127: 510 - 4d
Chiappe C.Pieraccini D.Zhao D.Fei Z.Dyson PJ. Adv. Synth. Catal. 2006, 348: 68 - 5a
Mowery ME.DeShong P. Org. Lett. 1999, 1: 2137 - 5b
Sahoo AK.Oda T.Nakao Y.Hiyama T. Adv. Synth. Catal. 2004, 346: 1715 - 5c
Shi SY.Zhang YH. J. Org. Chem. 2007, 72: 5927 - 6a
Wiskur SL.Korte A.Fu GC. J. Am. Chem. Soc. 2004, 126: 82 - 6b
Stanetty P.Hattinger G.Schnürch M.Mihovilovic MD. J. Org. Chem. 2005, 70: 5215 - 6c
Hadei N.Kantchev EAB.O’Brien CJ.Organ MG. J. Org. Chem. 2005, 70: 8503 - 6d
Huang Z.Qian M.Babinski DJ.Negishi E.-I. Organometallics 2005, 24: 475 - 6e
Xu H.Ekoue-Kovi K.Wolf C. J. Org. Chem. 2008, 73: 7638 - 6f
Sase S.Jaric M.Metzger A.Malakhov V.Knochel P. J. Org. Chem. 2008, 73: 7380 - 6g
Manolikakes G.Dong ZB.Mayr H.Li JS.Knochel P. Chem. Eur. J. 2009, 15: 1324 - 7a
Martin R.Fürstner A. Angew. Chem. Int. Ed. 2004, 43: 3955 - 7b
Nagano T.Hayashi T. Org. Lett. 2004, 6: 1297 - 7c
Yoshikai N.Mashima H.Nakamura E. J. Am. Chem. Soc. 2005, 127: 17978 - 7d
Bedford RB.Betham M.Bruce DW.Danopoulos AA.Frost RM.Hird M. J. Org. Chem. 2006, 71: 1104 - 7e
Leleu A.Fort Y.Schneider R. Adv. Synth. Catal. 2006, 348: 1086 - 7f
Wolf C.Xu HH. J. Org. Chem. 2008, 73: 162 - 7g
Manolikakes G.Knochel P. Angew. Chem. Int. Ed. 2009, 48: 205 - 7h
Hartmann CE.Nolan SP.Cazin CSJ. Organometallics 2009, 28: 2915 - 8a
Littke AF.Fu GC. Angew. Chem. Int. Ed. 2002, 41: 4176 - 8b
Hu Q.-S.Lu Y.Tang Z.-Y.Yu H.-B. J. Am. Chem. Soc. 2003, 125: 2856 - 8c
Bedford RB.Blake ME.Butts CP.Holder D. Chem. Commun. 2003, 466 - 8d
Miura M. Angew. Chem. Int. Ed. 2004, 43: 2201 - 8e
Zhou L.Miao Q.He R.Feng X.Bao M. Tetrahedron Lett. 2007, 48: 7899 - 8f
Hoshi T.Nakazawa T.Saitoh I.Mori A.Suzuki T.Sakai J.Hagiwara H. Org. Lett. 2008, 10: 2603 - 8g
So CM.Yeung CC.Lau CP.Kwong FY. J. Org. Chem. 2008, 73: 7803 - 9a
Munday RH.Martinelli JR.Buchwald SL. J. Am. Chem. Soc. 2008, 130: 2754 - 9b
Quasdorf KW.Tian X.Garg NK. J. Am. Chem. Soc. 2008, 130: 14422 - 9c
Tobisu M.Shimasaki T.Chatani N. Angew. Chem. Int. Ed. 2008, 47: 4866 - 9d
Guan B.-T.Wang Y.Li B.-J.Yu D.-G.Shi Z.-J. J. Am. Chem. Soc. 2008, 130: 14468 - 9e
Fors BP.Watson DA.Biscoe MR.Buchwald SL. J. Am. Chem. Soc. 2008, 130: 13552 - 9f
Li B.-J.Li Y.-Z.Lu X.-Y.Liu J.Guan B.-T.Shi Z.-J. Angew. Chem. Int. Ed. 2008, 47: 10124 - 9g
Ackermann L.Althammer A.Fenner S. Angew. Chem. Int. Ed. 2009, 48: 201 - 10a
Hartwig JF. Angew. Chem. Int. Ed. 1998, 37: 2046 - 10b
Huang X.Anderson KW.Zim D.Jiang L.Klapars A.Buchwald SL. J. Am. Chem. Soc. 2003, 125: 6653 - 10c
Chen Y.-J.Chen H.-H. Org. Lett. 2006, 8: 5609 - 10d
Hill LL.Moore LR.Huang RC.Craciun R.Vincent AJ.Dixon DA.Chou J.Woltermann CJ.Shaughnessy KH. J. Org. Chem. 2006, 71: 5117 - 10e
Biscoe MR.Fors BP.Buchwald SL. J. Am. Chem. Soc. 2008, 130: 6686 - 10f
Fors BP.Watson DA.Biscoe MR.Buchwald SL. J. Am. Chem. Soc. 2008, 130: 13552 - 10g
Zhu LB.Li GC.Luo L.Guo P.Lan JB.You JS. J. Org. Chem. 2009, 74: 2200 - 11a
Torraca KE.Huang X.Parrish CA.Buchwald SL. J. Am. Chem. Soc. 2001, 123: 10770 - 11b
Kataoka N.Shelby Q.Stambuli JP.Hartwig JF. J. Org. Chem. 2002, 67: 5553 - 11c
Vorogushin AV.Huang X.Buchwald SL. J. Am. Chem. Soc. 2005, 127: 8146 - 11d
Gooßen LJ.Gooßen K.Stanciu C. Angew. Chem. Int. Ed. 2009, 48: 3569 - 12a
Li GY. Angew. Chem. Int. Ed. 2001, 40: 1513 - 12b
Fernández-Rodríguez MA.Shen QL.Hartwig JF. Chem. Eur. J. 2006, 12: 7782 - 12c
Maitro G.Vogel S.Sadaoui M.Prestat G.Madec D.Poli G. Org. Lett. 2007, 9: 5493 - 13a
Wolfe JP.Singer RA.Yang BH.Buchwald SL. J. Am. Chem. Soc. 1999, 121: 9550 - 13b
Littke AF.Dai C.Fu GC. J. Am. Chem. Soc. 2000, 122: 4020 - 13c
Zapf A.Ehrentraut A.Beller M. Angew. Chem. Int. Ed. 2000, 39: 4153 - 13d
Bedford RB.Carzin C. SJ.Hazelwood SL. Angew. Chem. Int. Ed. 2002, 41: 4120 - 13e
Stambuli JP.Kuwano R.Hartwig JF. Angew. Chem. Int. Ed. 2002, 41: 4746 - 13f
Littke AF.Schwarz L.Fu GC. J. Am. Chem. Soc. 2002, 124: 6343 - 13g
So CM.Lau CP.Kwong FY. Org. Lett. 2007, 9: 2795 - 13h
So CM.Lau CP.Kwong FY. Angew. Chem. Int. Ed. 2008, 47: 8059 - 13i
Moore LR.Western EC.Craciun R.Spruell JM.Dixon DA.O’Halloran KP.Shaughnessy KH. Organometallics 2008, 27: 576 - 14a
Bourissou D.Guerret O.Gabbal FP.Bertrand G. Chem. Rev. 2000, 100: 39 - 14b
Jafarpour L.Nolan SP. Adv. Organomet. Chem. 2000, 46: 181 - 14c
Grasa GA.Viciu MS.Huang J.Zhang C.Trudell ML.Nolan SP. Organometallics 2002, 21: 2866 - 14d
Herrmann WA. Angew. Chem. Int. Ed. 2002, 41: 1291 - 14e
Altenhoff G.Goddard R.Lehmann CW.Glorius F. Angew. Chem. Int. Ed. 2003, 42: 3690 - 14f
Navarro O.Kelly RA.Nolan SP. J. Am. Chem. Soc. 2003, 125: 16194 - 14g
Wang J.-W.Meng F.-H.Zhang L.-F. Organometallics 2009, 28: 2334 - 15a
Wenkert E.Michelotti EL.Swindell CS. J. Am. Chem. Soc. 1979, 101: 2246 - 15b
Saito S.Sakai M.Miyaura N. Tetrahedron Lett. 1996, 37: 2993 - 15c
Dankwardt JW. Angew. Chem. Int. Ed. 2004, 43: 2428 - 15d
Percec V.Golding GM.Smidrkal J.Weichold O. J. Org. Chem. 2004, 69: 3474 - 15e
Xi Z.Liu B.Chen W. J. Org. Chem. 2008, 73: 3954 - 15f
Tobisu M.Shimasaki T.Chatani N. Angew. Chem. Int. Ed. 2008, 47: 4866 - 15g
Quasdorf KW.Tian X.Garg NK. J. Am. Chem. Soc. 2008, 130: 14422 - 16a
Zhu W.Ma DW. Org. Lett. 2006, 8: 261 - 16b
Li J.-H.Wang D.-P. Eur. J. Org. Chem. 2006, 2063 - 16c
Dubbaka SR.Kienle M.Mayr H.Knochel P. Angew. Chem. Int. Ed. 2007, 46: 9093 - 16d
Hintermann L.Xiao L.Aurélie L. Angew. Chem. Int. Ed. 2008, 47: 8246 - 17a
Fürstner A.Leitner A. Angew. Chem. Int. Ed. 2002, 41: 609 - 17b
Fürstner A.Leitner A.Mendez M.Krause H. J. Am. Chem. Soc. 2002, 124: 13856 - 17c
Sapountzis I.Lin WW.Kofink CC.Despotopoulou C.Knochel P. Angew. Chem. Int. Ed. 2005, 44: 1654 - 17d
Cahiez G.Habiak V.Duplais C.Moyeux A. Angew. Chem. Int. Ed. 2007, 46: 4364 - 17e
Kofink CC.Blank B.Pagano S.Götz N.Knochel P. Chem. Commun. 2007, 1954 - 17f
Bistri O.Correa A.Bolm C. Angew. Chem. Int. Ed. 2008, 47: 586 - 17g
Wen J.Zhang J.Chen S.-Y.Li J.Yu X.-Q. Angew. Chem. Int. Ed. 2008, 47: 8897 - 18a
Blum J.Gelman D.Baidossi W.Shakh E.Rosenfeld A.Aizenshtat Z. J. Org. Chem. 1997, 62: 8681 - 18b
Blum J.Berlin O.Milstein D.Ben-David Y.Wassermann BC.Schutte S.Schumann H. Synthesis 2000, 571 - 18c
Shenglof M.Gelman D.Molander GA.Blum J. Tetrahedron Lett. 2003, 44: 8593 - 19a
Negishi E.-I. Acc. Chem. Res. 1982, 15: 340 - 19b
Negishi E.-I.Takahashi T.Baba S.Van Horn DE.Okukado N. J. Am. Chem. Soc. 1987, 109: 2393 - 19c
Kessabi J.Beaudegnies R.Jung PMJ.Martin B.Monteel F.Wendeborg S. Org. Lett. 2006, 8: 5629 - 20a
Wu K.-H.Gau H.-M. J. Am. Chem. Soc. 2006, 128: 14808 - 20b
Hsieh S.-H.Chen C.-A.Chuang D.-W.Yang M.-C.Yang H.-T.Gau H.-M. Chirality 2008, 20: 924 - 20c
Zhou SL.Chuang D.-W.Chang S.-J.Gau H.-M. Tetrahedron: Asymmetry 2009, 20: 1407 - 21a
Chen C.-A.Wu K.-H.Gau H.-M. Angew. Chem. Int. Ed. 2007, 46: 5373 - 21b
Chen C.-A.Wu K.-H.Gau H.-M. Adv. Synth. Catal. 2008, 350: 1626 - 22
Ku S.-L.Hui X.-P.Chen C.-A.Kuo Y.-Y.Gau H.-M. Chem. Commun. 2007, 3847 - 23
Wu K.-H.Chuang D.-W.Chen C.-A.Gau H.-M. Chem. Commun. 2008, 2343 - 24
Biradar DB.Gau H.-M. Org. Lett. 2009, 11: 499 - 25
Zhou SL.Wu K.-H.Chen C.-A.Gau H.-M. J. Org. Chem. 2009, 74: 3500 - 26a
Rudolph J.Rasmussen T.Bolm C.Norrby P.-O. Angew. Chem. Int. Ed. 2003, 42: 3002 - 26b
Rudolph J.Bolm C.Norrby P.-O. J. Am. Chem. Soc. 2005, 127: 1548 - 27
Kuriyama M.Shimazawa R.Shirai R. Tetrahedron 2007, 63: 9393 - 28
Alacid E.Nájera C. Org. Lett. 2008, 10: 5011 - 29
Yang DX.Colletti SL.Wu K.Song M.Li GY.Shen HC. Org. Lett. 2009, 11: 381 - 30
Moon K.-S.Kim H.-J.Lee E.Lee M. Angew. Chem. Int. Ed. 2007, 46: 6807