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

Shigenari Kanemura; Azusa Kondoh; Hideki Yorimitsu; Koichiro Oshima

doi:10.1055/s-2008-1067193

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Synthesis 2008(16): 2659-2664
DOI: 10.1055/s-2008-1067193

SPECIALTOPIC

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

Shigenari Kanemura, Azusa Kondoh, Hideki Yorimitsu*, Koichiro Oshima*
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto-daigaku Katsura, Nishikyo-ku, Kyoto 615-8510, Japan
Fax: +81(75)3832438; e-Mail: yori@orgrxn.mbox.media.kyoto-u.ac.jp; e-Mail: oshima@orgrxn.mbox.media.kyoto-u.ac.jp;

Further Information

Publication History

Received 21 April 2008
Publication Date:
24 July 2008 (online)

Abstract
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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

References

For reviews, see:
1a Sugimura H. Okamura H. Miura M. Yoshida M. Takei H. Nippon Kagaku Kaishi 1985, 416

Google Scholar
1b Naso F. Pure Appl. Chem. 1988, 60: 79

Google Scholar
1c Fiandanese V. Pure Appl. Chem. 1990, 62: 1987

Google Scholar
1d Luh T.-Y. Acc. Chem. Res. 1991, 24: 257

Google Scholar
1e Dubbaka SR. Vogel P. Angew. Chem. Int. Ed. 2005, 44: 7674

Google Scholar
1f Prokopcová H. Kappe CO. Angew. Chem. Int. Ed. 2008, 47: 3674

Google Scholar
2a Okamura H. Miura M. Takei H. Tetrahedron Lett. 1979, 20: 43

Google Scholar
2b Takei H. Miura M. Sugimura H. Okamura H. Chem. Lett. 1979, 1447

Google Scholar
2c Takei H. Sugimura H. Miura M. Okamura H. Chem. Lett. 1980, 1209

Google Scholar
2d Okamura H. Takei H. Tetrahedron Lett. 1979, 20: 3425

Google Scholar
2e Wenkert E. Ferreira TW. Michelotti EL. J. Chem. Soc., Chem. Commun. 1979, 637

Google Scholar
2f Wenkert E. Fernandes JB. Michelotti EL. Swinndell CS. Synthesis 1983, 701

Google Scholar
2g Itami K. Mineno M. Muraoka N. Yoshida J. J. Am. Chem. Soc. 2004, 126: 11778

Google Scholar
2h Itami K. Yamazaki D. Yoshida J. J. Am. Chem. Soc. 2004, 126: 15396

Google Scholar
3 Kondoh A. Yorimitsu H. Oshima K. J. Am. Chem. Soc. 2007, 129: 4099

Crossref Google Scholar
4a Nishide K. Node M. J. Synth. Org. Chem., Jpn. 2004, 62: 895

Google Scholar
4b Node M. Kumar K. Nishide K. Ohsugi S. Miyamoto T. Tetrahedron Lett. 2001, 42: 9207

Google Scholar
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

Google Scholar
5b Kondoh A. Yorimitsu H. Oshima K. J. Org. Chem. 2005, 70: 6468

Google Scholar
6 Rout L. Sen TK. Punniyamurthy T. Angew. Chem. Int. Ed. 2007, 46: 5583

Crossref PubMed Google Scholar
7 Ajiki K. Hirano M. Tanaka K. Org. Lett. 2005, 7: 4193

Crossref PubMed Google Scholar
8 Comasseto JV. Lang ES. Tercio J. Ferreira B. Simonelli F. Correia VR. J. Organomet. Chem. 1987, 334: 329

Crossref Google Scholar
9 Zafrani Y. Gershonov E. Columbus I. J. Org. Chem. 2007, 72: 7014

Crossref Google Scholar
10 Kondolff I. Doucet H. Santelli M. Organometallics 2006, 25: 5219

Crossref Google Scholar
11 Haase M. Günther W. Görls H. Anders E. Synthesis 1999, 2071

Article in Thieme Connect Google Scholar
12 Kwong FY. Chan KS. Yeung CH. Chan ASC. Chem. Commun. 2004, 2336

Crossref Google Scholar
13 Powell DA. Fu GC. J. Am. Chem. Soc. 2004, 126: 7788

Crossref PubMed Google Scholar
14 Bedford RB. Betham M. Bruce DW. Danopoulos AA. Frost RA. Hird M. J. Org. Chem. 2006, 71: 1104

Crossref Google Scholar
15 Coxon JM. Schuyt HA. Steel PJ. Aust. J. Chem. 1980, 33: 1863

Crossref Google Scholar
16 Kitamura M. Kudo D. Narasaka K. ARKIVOC 2006, (iii): 148

Google Scholar
17 Protti S. Fagnoni M. Mella M. Albini A. J. Org. Chem. 2004, 69: 3465

Crossref PubMed Google Scholar
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

Google Scholar
19 Strotman NA. Sommer S. Fu GC. Angew. Chem. Int. Ed. 2007, 46: 3556

Crossref Google Scholar
20 Moussaoui Y. Saïd K. Salem RB. ARKIVOC 2006, (xii): 1

Google Scholar
21 Herve A. Rodriguez AL. Fouquet E. J. Org. Chem. 2005, 70: 1953

Crossref Google Scholar
22 Concellon JM. Rodriguez-Solla H. Simal C. Huerta M. Org. Lett. 2005, 7: 5833

Crossref PubMed Google Scholar
23 Hrubiec RT. Smith MB. Tetrahedron 1984, 40: 1457

Crossref Google Scholar
24 Satoh T. Kondo A. Musashi J. Tetrahedron 2004, 60: 5453

Crossref Google Scholar
25 Blue CD. Nelson DJ. J. Org. Chem. 1983, 48: 4538

Crossref Google Scholar
26 Goering HL. Seitz EP. Tseng CC. J. Org. Chem. 1981, 46: 5304

Crossref Google Scholar
27 Jang Y.-J. Yan M.-C. Lin Y.-F. Yao C.-F. J. Org. Chem. 2004, 69: 3961

Crossref PubMed Google Scholar
28 Hrubiec RT. Smith MB. Tetrahedron 1984, 40: 1457

Crossref Google Scholar
29 Fiandanese V. Marchese G. Naso F. Ronzini L. Synthesis 1987, 1034

Article in Thieme Connect Google Scholar
30 Hansen AL. Ebran J.-P. Gogsig TM. Skrydstrup T. J. Org. Chem. 2007, 72: 6464

Google Scholar