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

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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

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Referenzen

References

For reviews on Stille cross-coupling reactions, see:

<A NAME="RU25204ST-1A">1a</A> Stille JK. Angew. Chem., Int. Ed. Engl. 1986, 25: 508

<A NAME="RU25204ST-1B">1b</A> Farina V. Krishnamurthy V. Scott WJ. Org. React. 1997, 50: 1

<A NAME="RU25204ST-1C">1c</A> Littke AF. Fu GC. Angew. Chem. Int. Ed. 2002, 41: 4176 ; and references cited therein

<A NAME="RU25204ST-1D">1d</A> Netherton MR. Fu GC. Org. Lett. 2001, 3: 4295

<A NAME="RU25204ST-1E">1e</A> Espinet P. Echavarren AM. Angew. Chem. Int. Ed. 2004, 43: 4704

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

<A NAME="RU25204ST-2A">2a</A> 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

<A NAME="RU25204ST-2B">2b</A> Kadota I. Takamura H. Sato K. Ohno A. Matsuda K. Yamamoto Y. J. Am. Chem. Soc. 2003, 125: 46

<A NAME="RU25204ST-2C">2c</A> Boger DL. Ichikawa S. Jiang H. J. Am. Chem. Soc. 2000, 122: 12169

<A NAME="RU25204ST-3A">3a</A> Kosugi M. Sasazawa K. Shimizu Y. Migita T. Chem. Lett. 1977, 301

<A NAME="RU25204ST-3B">3b</A> Milstein D. Stille JK. J. Am. Chem. Soc. 1978, 100: 3636

<A NAME="RU25204ST-4A">4a</A> Nicolaou KC. Sorensen EJ. Classics in Total Synthesis VCH; New York: 1996. Chap. 31.

<A NAME="RU25204ST-4B">4b</A> For some very recent examples, see: Williams DR. Meyer KG. J. Am. Chem. Soc. 2001, 123: 765

<A NAME="RU25204ST-4C">4c</A> White JD. Carter RG. Sundermann KF. Wartmann M. J. Am. Chem. Soc. 2001, 123: 5407

<A NAME="RU25204ST-4D">4d</A> Liras S. Lynch CL. Fryer AM. Vu BT. Martin SF. J. Am. Chem. Soc. 2001, 123: 5918

<A NAME="RU25204ST-4E">4e</A> Hanessian S. Ma J. Wang W. J. Am. Chem. Soc. 2001, 123: 10200

<A NAME="RU25204ST-4F">4f</A> Smith AB. Minbiole KP. Verhoest PR. Schelhaas M. J. Am. Chem. Soc. 2001, 123: 10942

<A NAME="RU25204ST-5A">5a</A> Urgaonkar S. Su W. Verkade JG. Org. Lett. 2004, 6: 1421

<A NAME="RU25204ST-5B">5b</A> Littke AF. Fu GC. Angew. Chem. Int. Ed. 1999, 38: 2411

<A NAME="RU25204ST-5C">5c</A> Littke AF. Schwarz L. Fu GC. J. Am. Chem. Soc. 2002, 124: 6343

<A NAME="RU25204ST-5D">5d</A> Choudary BM. Madhi S. Chowdari NS. Kantam ML. Sreedhar B. J. Am. Chem. Soc. 2002, 124: 14127

<A NAME="RU25204ST-6A">6a</A> Grasa GA. Nolan SP. Org. Lett. 2001, 3: 119

<A NAME="RU25204ST-6B">6b</A> Crawforth CM. Fairlamb IJS. Taylor RJK. Tetrahedron Lett. 2004, 45: 461 ; and references cited therein

<A NAME="RU25204ST-7">7</A> Mee SPH. Lee V. Baldwin JE. Angew. Chem. Int. Ed. 2004, 43: 1132

<A NAME="RU25204ST-8A">8a</A> Yoshifuji M. Shima I. Inamoto N. Hirotsu K. Higuchi T. J. Am. Chem. Soc. 1981, 103: 4587

<A NAME="RU25204ST-8B">8b</A> Yoshifuji M. Shima I. Inamoto N. Hirotsu K. Higuchi T. J. Am. Chem. Soc. 1982, 104: 6167

<A NAME="RU25204ST-8C">8c</A> Yoshifuji M. J. Organomet. Chem. 2000, 611: 210

<A NAME="RU25204ST-8D">8d</A> Toyota K. Masaki K. Abe T. Yoshifuji M. Chem. Lett. 1995, 221

<A NAME="RU25204ST-8E">8e</A> Ikeda S. Ohhata F. Miyoshi M. Tanaka R. Minami T. Ozawa F. Yoshifuji M. Angew. Chem. Int. Ed. 2000, 39: 4512

<A NAME="RU25204ST-8F">8f</A> Ozawa F. Yamamoto S. Kawagishi S. Hiraoka M. Ikeda S. Minami T. Ito S. Yoshifuji M. Chem. Lett. 2001, 972

<A NAME="RU25204ST-8G">8g</A> Minami T. Okamoto H. Ikeda S. Tanaka R. Ozawa F. Yoshifuji M. Angew. Chem. Int. Ed. 2001, 40: 4501

<A NAME="RU25204ST-8H">8h</A> Ozawa F. Okamoto H. Kawagishi S. Yamamoto S. Minami T. Yoshifuji M. J. Am. Chem. Soc. 2002, 124: 10968

<A NAME="RU25204ST-8I">8i</A> Yoshifuji M. J. Synth. Org. Chem. Jpn. 2003, 61: 1116

<A NAME="RU25204ST-9A">9a</A> Mathey F. Angew. Chem. Int. Ed. 2003, 42: 1578

<A NAME="RU25204ST-9B">9b</A> Mathey F. J. Organomet. Chem. 2002, 646: 15

<A NAME="RU25204ST-9C">9c</A> Yoshifuji M. Phosphorus, Sulfur Silicon Relat. Elem. 2002, 177: 1827

<A NAME="RU25204ST-9D">9d</A> Le Floch P. Mathey F. Coord. Chem. Rev. 1998, 179: 771

<A NAME="RU25204ST-9E">9e</A> Yoshifuji M. J. Chem. Soc., Dalton Trans. 1998, 3343

<A NAME="RU25204ST-10A">10a</A> Appel R. Winkhaus V. Knoch F. Chem. Ber. 1997, 120: 243

<A NAME="RU25204ST-10B">10b</A> Yoshifuji M. Toyota K. Murayama M. Yoshimura H. Okamoto A. Hirotsu K. Nagase S. Chem. Lett. 1990, 2195

<A NAME="RU25204ST-10C">10c</A> Märkl G. Hennig R. Liebigs Ann. Chem. 1996, 2059

<A NAME="RU25204ST-10D">10d</A> Toyota K. Abe K. Horikawa K. Yoshifuji M. Bull. Chem. Soc. Jpn. 2004, 77: 1377

<A NAME="RU25204ST-10E">10e</A> Toyota K. Tashiro K. Yoshifuji M. Chem. Lett. 1991, 2079

<A NAME="RU25204ST-11A">11a</A> Gajare AS. Toyota K. Yoshifuji M. Ozawa F. Chem. Commun. 2004, 1994

<A NAME="RU25204ST-11B">11b</A> Gajare AS. Toyota K. Yoshifuji M. Ozawa F. J. Org. Chem. 2004, 69: 6504