Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2006(1): 0118-0120
DOI: 10.1055/s-2005-922765
DOI: 10.1055/s-2005-922765
LETTER
© Georg Thieme Verlag Stuttgart · New York
An Efficient Catalyst System for Palladium(0)-Catalyzed Cross-Coupling of Aryltrialkoxysilanes with Aryl Halides
Further Information
Received
26 October 2005
Publication Date:
16 December 2005 (online)
Publication History
Publication Date:
16 December 2005 (online)
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
- 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 ReactionsDiederich 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 ReactionsDiederich 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 ReactionsDiederich 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