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Synthesis 2008(16): 2659-2664
DOI: 10.1055/s-2008-1067193
DOI: 10.1055/s-2008-1067193
SPECIALTOPIC
© Georg Thieme Verlag
Stuttgart ˙ New York
Nickel-Catalyzed Cross-Coupling Reactions of Alkyl Aryl Sulfides and Alkenyl Alkyl Sulfides with Alkyl Grignard Reagents Using (Z)-3,3-Dimethyl-1,2-bis(diphenylphosphino)but-1-ene as Ligand
Weitere Informationen
Received
21 April 2008
Publikationsdatum:
24. Juli 2008 (online)
Publikationsverlauf
Publikationsdatum:
24. Juli 2008 (online)
![](https://www.thieme-connect.de/media/synthesis/200816/lookinside/thumbnails/10.1055-s-2008-1067193-1.jpg)
Abstract
A combination of nickel(II) acetylacetonate and (Z)-3,3-dimethyl-1,2-bis(diphenylphosphino)but-1-ene catalyzes cross-coupling reactions of alkyl aryl sulfides and alkenyl alkyl sulfides with alkyl Grignard reagents. Not only primary but also secondary alkyl Grignard reagents can be employed.
Key words
cross-coupling - nickel - sulfur - ligands - magnesium
- For reviews, see:
-
1a
Sugimura H.Okamura H.Miura M.Yoshida M.Takei H. Nippon Kagaku Kaishi 1985, 416 -
1b
Naso F. Pure Appl. Chem. 1988, 60: 79 -
1c
Fiandanese V. Pure Appl. Chem. 1990, 62: 1987 -
1d
Luh T.-Y. Acc. Chem. Res. 1991, 24: 257 -
1e
Dubbaka SR.Vogel P. Angew. Chem. Int. Ed. 2005, 44: 7674 -
1f
Prokopcová H.Kappe CO. Angew. Chem. Int. Ed. 2008, 47: 3674 -
2a
Okamura H.Miura M.Takei H. Tetrahedron Lett. 1979, 20: 43 -
2b
Takei H.Miura M.Sugimura H.Okamura H. Chem. Lett. 1979, 1447 -
2c
Takei H.Sugimura H.Miura M.Okamura H. Chem. Lett. 1980, 1209 -
2d
Okamura H.Takei H. Tetrahedron Lett. 1979, 20: 3425 -
2e
Wenkert E.Ferreira TW.Michelotti EL. J. Chem. Soc., Chem. Commun. 1979, 637 -
2f
Wenkert E.Fernandes JB.Michelotti EL.Swinndell CS. Synthesis 1983, 701 -
2g
Itami K.Mineno M.Muraoka N.Yoshida J. J. Am. Chem. Soc. 2004, 126: 11778 -
2h
Itami K.Yamazaki D.Yoshida J. J. Am. Chem. Soc. 2004, 126: 15396 - 3
Kondoh A.Yorimitsu H.Oshima K. J. Am. Chem. Soc. 2007, 129: 4099 -
4a
Nishide K.Node M. J. Synth. Org. Chem., Jpn. 2004, 62: 895 -
4b
Node M.Kumar K.Nishide K.Ohsugi S.Miyamoto T. Tetrahedron Lett. 2001, 42: 9207 - The ability of the dodecylthio group as a leaving group in cross-coupling reactions has scarcely been investigated, see:
-
5a
Miyazaki T.Han-ya Y.Tokuyama H.Fukuyama T. Synlett 2004, 477 -
5b
Kondoh A.Yorimitsu H.Oshima K. J. Org. Chem. 2005, 70: 6468 - 6
Rout L.Sen TK.Punniyamurthy T. Angew. Chem. Int. Ed. 2007, 46: 5583 - 7
Ajiki K.Hirano M.Tanaka K. Org. Lett. 2005, 7: 4193 - 8
Comasseto JV.Lang ES.Tercio J.Ferreira B.Simonelli F.Correia VR. J. Organomet. Chem. 1987, 334: 329 - 9
Zafrani Y.Gershonov E.Columbus I. J. Org. Chem. 2007, 72: 7014 - 10
Kondolff I.Doucet H.Santelli M. Organometallics 2006, 25: 5219 - 11
Haase M.Günther W.Görls H.Anders E. Synthesis 1999, 2071 - 12
Kwong FY.Chan KS.Yeung CH.Chan ASC. Chem. Commun. 2004, 2336 - 13
Powell DA.Fu GC. J. Am. Chem. Soc. 2004, 126: 7788 - 14
Bedford RB.Betham M.Bruce DW.Danopoulos AA.Frost RA.Hird M. J. Org. Chem. 2006, 71: 1104 - 15
Coxon JM.Schuyt HA.Steel PJ. Aust. J. Chem. 1980, 33: 1863 - 16
Kitamura M.Kudo D.Narasaka K. ARKIVOC 2006, (iii): 148 - 17
Protti S.Fagnoni M.Mella M.Albini A. J. Org. Chem. 2004, 69: 3465 - 18
Oosterbaan WD.van Gerven PCM.van Walree CA.Koeberg M.Piet JJ.Havenith RWA.Zwikker JW.Jenneskens LW.Gleiter R. Eur. J. Org. Chem. 2003, 3117 - 19
Strotman NA.Sommer S.Fu GC. Angew. Chem. Int. Ed. 2007, 46: 3556 - 20
Moussaoui Y.Saïd K.Salem RB. ARKIVOC 2006, (xii): 1 - 21
Herve A.Rodriguez AL.Fouquet E. J. Org. Chem. 2005, 70: 1953 - 22
Concellon JM.Rodriguez-Solla H.Simal C.Huerta M. Org. Lett. 2005, 7: 5833 - 23
Hrubiec RT.Smith MB. Tetrahedron 1984, 40: 1457 - 24
Satoh T.Kondo A.Musashi J. Tetrahedron 2004, 60: 5453 - 25
Blue CD.Nelson DJ. J. Org. Chem. 1983, 48: 4538 - 26
Goering HL.Seitz EP.Tseng CC. J. Org. Chem. 1981, 46: 5304 - 27
Jang Y.-J.Yan M.-C.Lin Y.-F.Yao C.-F. J. Org. Chem. 2004, 69: 3961 - 28
Hrubiec RT.Smith MB. Tetrahedron 1984, 40: 1457 - 29
Fiandanese V.Marchese G.Naso F.Ronzini L. Synthesis 1987, 1034 - 30
Hansen AL.Ebran J.-P.Gogsig TM.Skrydstrup T. J. Org. Chem. 2007, 72: 6464