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Synthesis 2012(7): 1030-1036
DOI: 10.1055/s-0031-1289723
DOI: 10.1055/s-0031-1289723
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Cu(acac)2-Catalyzed Synthesis of Functionalized Bis(arylmethyl)zinc Reagents and Their Olefination Reaction with Aromatic Aldehydes
Weitere Informationen
Received
17 December 2011
Publikationsdatum:
24. Februar 2012 (online)
Publikationsverlauf
Publikationsdatum:
24. Februar 2012 (online)
Abstract
An efficient and facile copper(II) acetylacetonate catalyzed synthesis of functionalized bis(arylmethyl)zinc reagents from arylmethyl halides and their olefination reaction with aromatic aldehydes is reported. Aluminum trichloride was found to be the key ingredient in these reactions and (E)-stilbenes were obtained in high yields.
Key words
aldehyde - zinc - nucleophilic addition - olefination - benzylation
-
1a
The Chemistry of Organozinc Compounds
Rappoport Z.Marek I. John Wiley & Sons; Chichester: 2006. -
1b
Knochel P.Jones P. Organozinc Reagents, A Practical Approach Oxford University Press; Oxford: 1999. -
1c
Erdik E. Organozinc Reagents in Organic Synthesis CRC Press; New York: 1996. -
1d
Knochel P. Handbook of Functionalized Organometallics Wiley-VCH; Weinheim: 2005. Chap. 7. -
2a
Wang J.-X.Fu Y.Hu YL. Angew. Chem. Int. Ed. 2002, 41: 2757 -
2b
Wang J.-X.Fu Y.Hu YL. Synthesis 2003, 1506 -
2c
Wang J.-X.Wang K.Zhao L.Li H.Fu Y.Hu Y. Adv. Synth. Catal. 2006, 348: 1262 - 3
Knochel P. Synlett 1995, 393 - 4
Frankland E. Justus Liebigs Ann. Chem. 1849, 71: 171 - 5
Rozema MJ.Sidduri A.Knochel P. J. Org. Chem. 1992, 57: 1956 -
6a
Langer F.Schwink L.Devasagayaraj A.Chavant P.-Y. J. Org. Chem. 1996, 61: 8229 -
6b
Boudier A.Darcel C.Flachsmann F.Micouin L.Oestreich M.Knochel P. Chem. Eur. J. 2000, 6: 2748 -
6c
Hupe E.Calaza MI.Knochel P. Chem. Eur. J. 2003, 9: 2789 -
7a
Klement I.Lütjens H.Knochel P. Tetrahedron Lett. 1995, 36: 3161 -
7b
Gao Y.Urabe H.Sato F. J. Org. Chem. 1994, 59: 5521 -
8a
Nützel K. Houben--Weyl 4th Ed., Vol. 13/2a: Georg Thieme Verlag; Stuttgart: 1973. p.552 -
8b
Von dem Bussche-Hünnefeld JL.Seebach D. Tetrahedron 1992, 48: 5719 -
8c
Murakami K.Yorimitsu H.Oshima K. Chem. Eur. J. 2010, 16: 7688 -
8d
Luche J.-L.Petrier C.Lansard J.-P.Greene AE. J. Org. Chem. 1983, 48: 3837 -
8e
Luzung MR.Patel JS.Yin J. J. Org. Chem. 2010, 75: 8330 -
9a
Metzger A.Bernhardt S.Manolikakes G.Knochel P. Angew. Chem. Int. Ed. 2010, 49: 4665 -
9b
Buesking AW.Baguley TD.Ellman JA. Org. Lett. 2011, 13: 964 -
9c
Metzger A.Piller FM.Knochel P. Chem. Commun. 2008, 5824 - 10
Buesking AW.Baguley TD.Ellman JA. Org. Lett. 2011, 13: 964 - 11
Eastham JF.Cannon DY. J. Org. Chem. 1960, 25: 1504 - 12
Peng Z.-Y.Ma F.-F.Zhu L.-F.Xie X.-M.Zhang Z.
J. Org. Chem. 2009, 74: 6855 - 13
Knoess HP.Furlong MT.Rozema MJ.Knochel P.
J. Org. Chem. 1991, 56: 5974 - 14
Sugihara T.Satoh T.Miura M.Nomura M. Adv. Synth. Catal. 2004, 346: 1765 - 15
Wadsworth WS.Emmons WD. J. Am. Chem. Soc. 1961, 83: 1733 - 16
Yasuda M.Isami T.Kubo J.Mizutani M.Yamashita T.Shima K. J. Org. Chem. 1992, 57: 1351 - 17
Chhor RB.Singh KA.Nosse B.Tandon VK. Synth. Commun. 2003, 33: 2519 - 18
Kim C.-B.Cho C.-H.Jo MJ.Park K. Bull. Korean Chem. Soc. 2011, 32: 3655 - 19
von Walter R.Wetzlich A. J. Prakt. Chem. 1900, 61: 169 - 20
Ruasse MF.Dubois JE. J. Org. Chem. 1972, 37: 1770