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Volumn 130, Issue 34, 2008, Pages 11270-11271

A general and highly selective chelate-controlled intermolecular oxidative heck reaction

Author keywords

[No Author keywords available]

Indexed keywords

CHELATE; PALLADIUM; SULFOXIDE;

EID: 50249111638     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja804120r     Document Type: Article
Times cited : (189)

References (36)
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    • For reviews, see: (a) Bräse, S.; deMeijere, A. Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: New York, 2004; Chapter 5.
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    • Disubstituted alkenes: (b) Gürtler, C.; Buchwald, S. L. Chem. Eur. J. 1999, 5, 3107.
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    • Internal olefins react poorly in our system Supporting Information
    • (c) Internal olefins react poorly in our system (Supporting Information).
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    • Our discovery of the acetate directing effect for the Heck appears general: (b) Pan, D, Chen, A, Su, Y, Zhou, W, Li, S, Jia, W, Xiao, J, Liu, Q, Zhang, L, Jiao, N. Angew. Chem, Int. Ed. 2008, 47, 4729
    • Our discovery of the acetate directing effect for the Heck appears general: (b) Pan, D.; Chen, A.; Su, Y.; Zhou, W.; Li, S.; Jia, W.; Xiao, J.; Liu, Q.; Zhang, L.; Jiao, N. Angew. Chem., Int. Ed. 2008, 47, 4729.
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    • 2 with cationic Pd: (a) Nishikata, T.; Yamamoto, Y.; Miyaura, N. Angew. Chem., Int. Ed. 2003, 42, 2768.
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    • 1 catalyzes C-H oxidation and animations: (b) Chen, M. S.; Prabagaran, N.; Labenz, N. A.; White, M. C. J. Am. Chem. Soc. 2005, 127, 6970.
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    • 3 coupled in 60% yield (see Supporting Information).
    • 3 coupled in 60% yield (see Supporting Information).
  • 34
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    • Boric acid is likely a fluoride acceptor that opens a p-orbital on the aryl boron for transmetallation. For a review of these reagents, see: Molander, G. A, Ellis, N. Acc. Chem. Res. 2007, 40, 275. and references therein
    • Boric acid is likely a fluoride acceptor that opens a p-orbital on the aryl boron for transmetallation. For a review of these reagents, see: Molander, G. A.; Ellis, N. Acc. Chem. Res. 2007, 40, 275. and references therein.
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    • 2 + DHQ). For an important study on PdH in Heck reactions, see: Hills, I. D.; Fu, G. C. J. Am. Chem. Soc. 2004, 126, 13178.
    • 2 + DHQ). For an important study on PdH in Heck reactions, see: Hills, I. D.; Fu, G. C. J. Am. Chem. Soc. 2004, 126, 13178.


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