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Synlett 2003(6): 0882-0884
DOI: 10.1055/s-2003-38755
DOI: 10.1055/s-2003-38755
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York
Phosphine-Free Suzuki-Miyaura Reactions Catalyzed by Bishydrazone-Pd-Complex
Further Information
Received
4 March 2003
Publication Date:
17 April 2003 (online)
Publication History
Publication Date:
17 April 2003 (online)
Abstract
Glyoxal bis(methylphenylhydrazone) 1 was prepared and examined as a ligand for the Suzuki-Miyaura cross-coupling reaction of aryl bromides and arylboronic acids. We found phosphine-free catalyst, such as Pd(OAc)2/hydrazone ligand 1 to be an efficient catalyst for a variety of substrates to produce the coupling products in good yields at room temperature.
Key words
hydrazone - Suzuki-Miyaura reaction - cross-coupling - palladium - phosphine-free
- For reviewes, see:
-
1a
Miyaura N.Suzuki A. Chem. Rev. 1995, 95: 2457 -
1b
Stanforth SP. Tetrahedron 1998, 54: 263 -
1c
Suzuki A. Metal-Catalyzed Cross-Coupling ReactionsDiederich F.Stang PJ. Wiley-VCH; Weinheim: 1998. p.49 -
1d
Suzuki A. J. Orgmet. Chem. 1999, 576: 147 -
1e
Llord-Williams P.Giralt E. Chem. Soc. Rev. 2001, 30: 145 - For examples, see:
-
2a
Patel M.Rodgers JD.McHugh RJ.Johnson BL.Cordova BC.Klabe RM.Bacheler LT.Erickson-Viitanen S.Ko SS. Bioorg. Med. Chem. Lett. 1999, 9: 3217 -
2b
Wang W.Xiong C.Yang J.Hruby VJ. Terahedron Lett. 2001, 42: 7717 -
2c
Vaz B.Rosana R.Nieto M.Paniello AI.de Lera AR. Terahedron Lett. 2001, 42: 7409 -
2d
Schomaker JM.Delia TJ. J. Org. Chem 2001, 66: 7125 -
2e
Wong K.-T.Huang TS.Lin Y.Wu C.-C.Lee G.-H.Peng S.-M.Chou CH.Su YO. Org. Lett. 2002, 4: 513 - For examples, see:
-
3a
Hobbs PD.Upender V.Dawson MI. Synlett 1997, 965 -
3b
Nicolaou KC.Li H.Boddy CNC.Ramanjulu JM.Yue T.-Y.Natarajan S.Chu X.-J.Brase S.Rubsam F. Chem.-Eur. J. 1999, 5: 2584 -
3c
Nicolaou KC.Koumbis AE.Takayanagi M.Natarajan S.Jain NF.Bando T.Li H.Hughes R. Chem.-Eur. J. 1999, 5: 2622 -
3d
Kamikawa K.Watanabe T.Daimon A.Uemura M. Tetrahedron 2000, 56: 2325 -
4a
Littke AF.Fu GC. Angew. Chem. Int. Ed. 1998, 37: 3387 -
4b
Littke AF.Dai C.Fu GC. J. Am. Chem. Soc. 2000, 122: 4020 -
5a
Herrmann WA.Elison M.Fischer J.Kocher C.Artus GRJ. Angew. Chem., Int. Ed. Engl. 1995, 34: 2371 -
5b
Weskamp T.Bohm VPW.Herrmann WA. J. Orgmet. Chem. 1999, 585: 348 -
5c
Bohm VPW.Gstottmayr CWK.Weskamp T.Herrmann WA. J. Orgmet. Chem. 2000, 595: 186 -
5d
Zhang C.Huang J.Trudell ML.Nolan SP. J. Org. Chem. 1999, 64: 3804 -
5e
Zhang C.Trudell ML. Tetrahedron Lett. 2000, 41: 595 -
6a
Weissan H.Milstein D. Chem. Commun. 1999, 1901 -
6b
Bedford RB.Cazin CSJ. Chem. Commun. 2001, 1540 -
7a
Alonso DA.Najera C.Pacheco MC. Org. Lett. 2000, 2: 1823 -
7b
Botella L.Najera C. Angew. Chem. Int. Ed. 2002, 41: 179 - 8
Grasa GA.Hillier AC.Nolan SP. Org. Lett. 2001, 3: 1077 - 9
Tao B.Boykin DW. Terahedron Lett. 2002, 43: 4955 -
10a
Bombieri G.Caglioti L.Cattalini L.Forsellini E.Gasparrini F.Graziani R.Vigato PA. J. Chem. Soc., Chem. Commun. 1971, 1415 -
10b
Maresca L.Natile G.Cattalini L.Gasparrini F. J. Chem. Soc., Dalton Trans. 1975, 1602 -
10c
Mino T.Imiya W.Yamashita M. Synlett 1997, 583 -
10d
Bacchi A.Carcelli M.Pelagatti P.Pelizzi C.Pelizzi G.Salati C.Sgarabotto P. Inorg. Chim. Acta 1999, 295: 171 -
10e
Mino T.Shiotsuki M.Yamamoto N.Suenaga T.Sakamoto M.Fujita T.Yamashita M. J. Org. Chem. 2001, 66: 1795 ; and references cited therein