An Efficient Catalyst System for Palladium(0)-Catalyzed Cross-Coupling of Aryltrialkoxysilanes with Aryl Halides

Miki Murata; Syo Yoshida; Shin-ichiro Nirei; Shinji Watanabe; Yuzuru Masuda

doi:10.1055/s-2005-922765

LETTER

An Efficient Catalyst System for Palladium(0)-Catalyzed Cross-Coupling of Aryltrialkoxysilanes with Aryl Halides

Miki Murata*, Syo Yoshida, Shin-ichiro Nirei, Shinji Watanabe, Yuzuru Masuda
Department of Materials Science, Kitami Institute of Technology, Kitami, 090-8507, Japan
Fax: +81(157)264973; e-Mail: muratamk@mail.kitami-it.ac.jp;

Abstract

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Abstract

A combination of Pd(dba)₂ and a bisphosphine ligand, bis(2-diisopropylphosphinophenyl)ether, has proven to be general and efficient in fluoride-induced cross-coupling of aryltrialkoxysilanes with aryl halides. The substrate scope is broad and includes a variety of aryl bromides and chlorides.

Key words

silicon - palladium - catalysis - cross-coupling - biaryls

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References

References and Notes

For reviews, 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 Mitchell TN. In Metal-Catalyzed Cross-Coupling Reactions Diederich F. Stang PJ. Wiley-VCH; Weinheim: 1998. p.167

For reviews, see:

2a Miyaura N. Suzuki A. Chem. Rev. 1995, 95: 2457

2b Suzuki A. In Metal-Catalyzed Cross-Coupling Reactions Diederich F. Stang PJ. Wiley-VCH; Weinheim: 1998. p.49

2c Miyaura N. Adv. Organomet. Chem. 1998, 6: 187

For reviews, see:

3a Hatanaka Y. Hiyama T. Synlett 1991, 845

3b Hiyama T. In Metal-Catalyzed Cross-Coupling Reactions Diederich F. Stang PJ. Wiley-VCH; Weinheim: 1998. p.421

3c Hiyama T. Shirakawa E. Top. Curr. Chem. 2002, 219: 61

4a Shibata K. Miyazawa K. Goto Y. Chem. Commun. 1997, 1309

4b Mowery ME. DeShong P. J. Org. Chem. 1999, 64: 1684

4c Mowery ME. DeShong P. Org. Lett. 1999, 1: 2137

4d Lee HM. Nolan SP. Org. Lett. 2000, 2: 2053

4e Murata M. Shimazaki R. Watanabe S. Masuda Y. Synthesis 2001, 2231

4f Wolf C. Lerebours R. Org. Lett. 2004, 6: 1147

4g Lerebours R. Wolf C. Synthesis 2005, 2287

For the synthetic route to aryltrialkoxysilanes, see:

5a Murata M. Suzuki K. Watanabe S. Masuda Y. J. Org. Chem. 1997, 62: 8569

5b Manoso AS. DeShong P. J. Org. Chem. 2001, 66: 7455

5c Murata M. Ishikura M. Nagata M. Watanabe S. Masuda Y. Org. Lett. 2002, 4: 1843

5d Komuro K. Ishizaki K. Suzuki H. Touagousei-kenkyu-nenpo 2003, 6: 24

6 For modified Negishi biaryl coupling using DPPF ligand, see: Gauthier DR. Szumigala RH. Dormer PG. Armstrong JD. Volante RP. Reider PJ. Org. Lett. 2002, 4: 375

7 For Suzuki-Miyaura biaryl coupling using DPEphos ligand, see: Yin J. Rainka MP. Zhang X.-X. Buchwald SL. J. Am. Chem. Soc. 2002, 124: 1162

8 i-Pr-DPEphos (L8) was prepared from diphenylether and (i-Pr)₂PCl by a similar procedure for the preparation of DPEphos. See: Kranenburg M. Vanderburgt YEM. Kamer PCJ. van Leeuwen PWNM. Goubitz K. Fraanje J. Organometallics 1995, 14: 3081

9 For a review on palladium-catalyzed couplings of aryl chlorides, see: Littke AF. Fu GC. Angew. Chem. Int. Ed. 2002, 41: 4176