Low-Coordinated Diphosphinidenecyclobutene Ligands: A New Entry for Stille Cross-Coupling of Aryl Bromides

Anil S. Gajare; Rader S. Jensen; Kozo Toyota; Masaaki Yoshifuji; Fumiyuki Ozawa

doi:10.1055/s-2004-836023

LETTER

Low-Coordinated Diphosphinidenecyclobutene Ligands: A New Entry for Stille Cross-Coupling of Aryl Bromides

Anil S. Gajare^a, Rader S. Jensen^a, Kozo Toyota^a, Masaaki Yoshifuji*^a, Fumiyuki Ozawa^b
^a Department of Chemistry, Graduate School of Science, Tohoku University, Aoba, Sendai 980-8578, Japan
^b Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan
Fax: +81(22)2176562; e-Mail: yoshifj@mail.tains.tohoku.ac.jp;

Abstract

Alle Artikel dieser Rubrik

Abstract

A sterically protected diphosphinidenecyclobutene/palladium system has been used to mediate the catalytic cross-coupling of aryl bromides with organostannanes. An air- and moisture-stable diphosphinidenecyclobutene ligand proved the efficiency and generality of this class of ligand for cross-coupling reactions.

Key words

Stille cross-coupling - diphosphinidenecyclobutene - palladium - aryl bromides

Volltext

Referenzen

References

For reviews on Stille cross-coupling reactions, see:

1a Stille JK. Angew. Chem., Int. Ed. Engl. 1986, 25: 508

1b Farina V. Krishnamurthy V. Scott WJ. Org. React. 1997, 50: 1

1c Littke AF. Fu GC. Angew. Chem. Int. Ed. 2002, 41: 4176 ; and references cited therein

1d Netherton MR. Fu GC. Org. Lett. 2001, 3: 4295

1e Espinet P. Echavarren AM. Angew. Chem. Int. Ed. 2004, 43: 4704

For applications of the Stille reaction in natural product synthesis, see:

2a Nicolaou KC. Li Y. Sugita K. Monenschein H. Guntupalli P. Mitchell HJ. Fylaktakidou KC. Vourloumis D. Giannakakou P. O’Brate A. J. Am. Chem. Soc. 2003, 125: 15443

2b Kadota I. Takamura H. Sato K. Ohno A. Matsuda K. Yamamoto Y. J. Am. Chem. Soc. 2003, 125: 46

2c Boger DL. Ichikawa S. Jiang H. J. Am. Chem. Soc. 2000, 122: 12169

3a Kosugi M. Sasazawa K. Shimizu Y. Migita T. Chem. Lett. 1977, 301

3b Milstein D. Stille JK. J. Am. Chem. Soc. 1978, 100: 3636

4a Nicolaou KC. Sorensen EJ. Classics in Total Synthesis VCH; New York: 1996. Chap. 31.

4b For some very recent examples, see: Williams DR. Meyer KG. J. Am. Chem. Soc. 2001, 123: 765

4c White JD. Carter RG. Sundermann KF. Wartmann M. J. Am. Chem. Soc. 2001, 123: 5407

4d Liras S. Lynch CL. Fryer AM. Vu BT. Martin SF. J. Am. Chem. Soc. 2001, 123: 5918

4e Hanessian S. Ma J. Wang W. J. Am. Chem. Soc. 2001, 123: 10200

4f Smith AB. Minbiole KP. Verhoest PR. Schelhaas M. J. Am. Chem. Soc. 2001, 123: 10942

5a Urgaonkar S. Su W. Verkade JG. Org. Lett. 2004, 6: 1421

5b Littke AF. Fu GC. Angew. Chem. Int. Ed. 1999, 38: 2411

5c Littke AF. Schwarz L. Fu GC. J. Am. Chem. Soc. 2002, 124: 6343

5d Choudary BM. Madhi S. Chowdari NS. Kantam ML. Sreedhar B. J. Am. Chem. Soc. 2002, 124: 14127

6a Grasa GA. Nolan SP. Org. Lett. 2001, 3: 119

6b Crawforth CM. Fairlamb IJS. Taylor RJK. Tetrahedron Lett. 2004, 45: 461 ; and references cited therein

7 Mee SPH. Lee V. Baldwin JE. Angew. Chem. Int. Ed. 2004, 43: 1132

8a Yoshifuji M. Shima I. Inamoto N. Hirotsu K. Higuchi T. J. Am. Chem. Soc. 1981, 103: 4587

8b Yoshifuji M. Shima I. Inamoto N. Hirotsu K. Higuchi T. J. Am. Chem. Soc. 1982, 104: 6167

8c Yoshifuji M. J. Organomet. Chem. 2000, 611: 210

8d Toyota K. Masaki K. Abe T. Yoshifuji M. Chem. Lett. 1995, 221

8e Ikeda S. Ohhata F. Miyoshi M. Tanaka R. Minami T. Ozawa F. Yoshifuji M. Angew. Chem. Int. Ed. 2000, 39: 4512

8f Ozawa F. Yamamoto S. Kawagishi S. Hiraoka M. Ikeda S. Minami T. Ito S. Yoshifuji M. Chem. Lett. 2001, 972

8g Minami T. Okamoto H. Ikeda S. Tanaka R. Ozawa F. Yoshifuji M. Angew. Chem. Int. Ed. 2001, 40: 4501

8h Ozawa F. Okamoto H. Kawagishi S. Yamamoto S. Minami T. Yoshifuji M. J. Am. Chem. Soc. 2002, 124: 10968

8i Yoshifuji M. J. Synth. Org. Chem. Jpn. 2003, 61: 1116

9a Mathey F. Angew. Chem. Int. Ed. 2003, 42: 1578

9b Mathey F. J. Organomet. Chem. 2002, 646: 15

9c Yoshifuji M. Phosphorus, Sulfur Silicon Relat. Elem. 2002, 177: 1827

9d Le Floch P. Mathey F. Coord. Chem. Rev. 1998, 179: 771

9e Yoshifuji M. J. Chem. Soc., Dalton Trans. 1998, 3343

10a Appel R. Winkhaus V. Knoch F. Chem. Ber. 1997, 120: 243

10b Yoshifuji M. Toyota K. Murayama M. Yoshimura H. Okamoto A. Hirotsu K. Nagase S. Chem. Lett. 1990, 2195

10c Märkl G. Hennig R. Liebigs Ann. Chem. 1996, 2059

10d Toyota K. Abe K. Horikawa K. Yoshifuji M. Bull. Chem. Soc. Jpn. 2004, 77: 1377

10e Toyota K. Tashiro K. Yoshifuji M. Chem. Lett. 1991, 2079

11a Gajare AS. Toyota K. Yoshifuji M. Ozawa F. Chem. Commun. 2004, 1994

11b Gajare AS. Toyota K. Yoshifuji M. Ozawa F. J. Org. Chem. 2004, 69: 6504