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Synthesis 2003(5): 0780-0784
DOI: 10.1055/s-2003-38060
DOI: 10.1055/s-2003-38060
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart ˙ New York
Palladium-Catalyzed Carbonylative Coupling Reactions Using Triorganoindium Compounds
Further Information
Received
15 February 2003
Publication Date:
21 March 2003 (online)
Publication History
Publication Date:
21 March 2003 (online)
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Abstract
A novel palladium-catalyzed carbonylative cross-coupling reaction that employs triorganoindium compounds is described. The reaction proceeds under a carbon monoxide atmosphere with alkyl-, alkynyl-, and arylindium reagents to give good yields of unsymmetrical ketones with high atom economy. All three organic groups attached to the metal are efficiently transferred in this carbonylative coupling reaction.
Key words
atom economy - indium - carbonylative cross-coupling - organometallic reagents - palladium catalysis
-
1a
Cintas P. Synlett 1995, 1087 -
1b
Marshall JA. Chemtracts: Org. Chem. 1997, 10: 481 -
1c
Li C.-J.Chan T.-H. Organic Reactions in Aqueous Media Wiley; New York: 1997. Chap. 4. p.64-114 -
1d
Paquette LA. In Green Chemistry: Frontiers in Benign Chemical Synthesis and ProcessingAnastas PT.Williamson TC. Oxford University Press; Oxford: 1998. Chap. 15. p.250-264 -
2a
Li C.-J.Chan T.-H. Tetrahedron 1999, 55: 11149 -
2b
Ranu BC. Eur. J. Org. Chem. 2000, 2347 -
2c
Pae AN.Cho YS. Curr. Org. Chem. 2002, 6: 715 -
3a
Araki S.Shimizu K.Jin S.-J.Butsugan Y. J. Chem. Soc., Chem. Commun. 1991, 824 -
3b
Pérez I.Pérez Sestelo J.Maestro MA.Mouriño A.Sarandeses LA. J. Org. Chem. 1998, 63: 10074 - For contributions from our group, see:
-
4a
Pérez I.Pérez Sestelo J.Sarandeses LA. Org. Lett. 1999, 1: 1267 -
4b
Pérez I.Pérez Sestelo J.Sarandeses LA. J. Am. Chem. Soc. 2001, 123: 4155 -
4c
Pena MA.Pérez I.Pérez Sestelo J.Sarandeses LA. Chem. Commun. 2002, 2246 -
5a
Nomura R.Miyazaki S.-I.Matsuda H. J. Am. Chem. Soc. 1992, 114: 2738 -
5b
Takami K.Yorimitsu H.Shinokubo H.Matsubara S.Oshima K. Org. Lett. 2001, 3: 1997 -
5c
Lee PH.Sung S.Lee K. Org. Lett. 2001, 3: 3201 -
5d
Gotov B.Kaufmann J.Schumann H.Schmalz H.-G. Synlett 2002, 361 -
5e
Jaber N.Gelman D.Schumann H.Dechert S.Blum J. Eur. J. Org. Chem. 2002, 1628 -
5f
Lee K.Lee J.Lee PH. J. Org. Chem. 2002, 67: 8265 -
5g
Lee K.Seomoon D.Lee PH. Angew. Chem. Int. Ed. 2002, 41: 3901 -
6a
Araki S.Imai A.Shimizu K.Yamada M.Mori A.Butsugan Y. J. Org. Chem. 1995, 60: 1841 -
6b
Ranu BC.Majee A. Chem. Commun. 1997, 1225 -
6c
Fujiwara N.Yamamoto Y. J. Org. Chem. 1999, 64: 4095 -
6d
Klaps E.Schmid W. J. Org. Chem. 1999, 64: 7537 -
6e
Takami K.Yorimitsu H.Oshima K. Org. Lett. 2002, 4: 2993 -
7a
Lee PH.Sung S.-Y.Lee K.Chang S. Synlett 2002, 146 -
7b
Rodríguez, D.; Pérez Sestelo, J.; Sarandeses, L. A. J. Org. Chem. 2003, 68, in press.
-
8a
Thompson DJ. In Comprehensive Organic Synthesis Vol. 3:Trost BM.Fleming I. Pergamon; Oxford: 1991. p.1015-1043 -
8b
Bates RW. In Comprehensive Organometallic Chemistry II Vol. 12:Abel EW.Stone FGA.Wilkinson G. Pergamon; Oxford: 1995. p.349-386 -
9a
Goure WF.Wright ME.Davis PD.Labadie SS.Stille JK. J. Am. Chem. Soc. 1984, 106: 6417 -
9b
Crisp GT.Scott WJ.Stille JK. J. Am. Chem. Soc. 1984, 106: 7500 -
9c
Echavarren AM.Stille JK. J. Am. Chem. Soc. 1988, 110: 1557 -
10a
Wakita Y.Yasunaga T.Akita M.Kojima M. J. Organomet. Chem. 1986, 301: C17 -
10b
Kondo T.Tsuji J.Watanabe Y. J. Organomet. Chem. 1988, 345: 397 -
10c
Crigg R.Redpath J.Sridharan V.Wilson D. Tetrahedron Lett. 1994, 35: 7661 -
10d
Ishiyama T.Kizaki H.Hayashi T.Suzuki A.Miyaura N. J. Org. Chem. 1998, 63: 4726 -
11a
Bumagin NA.Ponomaryov AB.Beletskaya IP. Tetrahedron Lett. 1985, 26: 4819 -
11b
Wakita Y.Yasunaga T.Kojima M. J. Organomet. Chem. 1985, 288: 261 - 12
Tamaru Y.Ochiai H.Yamada Y.Yashida Z. Tetrahedron Lett. 1983, 24: 3869 - 13
Araki S.Shimizu T.Butsugan Y. Chem. Express 1991, 6: 583 - 15
Nozaki K.Sato N.Takaya H. J. Org. Chem. 1994, 59: 2679 - 16
Zhu L.Wehmeyer RM.Rieke RD. J. Org. Chem. 1991, 56: 1445 - 17
Huang Y.-C.Majumdar KK.Cheng C.-H. J. Org. Chem. 2002, 67: 1682 - 18
Kang S.-K.Lim K.-H.Ho P.-S.Kim W.-Y. Synthesis 1997, 874
References
Commercially available.