Pd(0)/PR3-catalyzed intermolecular arylation of sp3 C-H bonds
- PMID: 19580277
- PMCID: PMC2727875
- DOI: 10.1021/ja903573p
Pd(0)/PR3-catalyzed intermolecular arylation of sp3 C-H bonds
Abstract
Pd(0)-catalyzed intermolecular arylation of sp(3) C-H bonds has been achieved using PR(3)/ArI. This protocol can be used to arylate a variety of aliphatic carboxylic acid derivatives, including a number of bioactive drug molecules. The use of fluorinated aryl iodides also allows for the introduction of fluorine into a molecule of interest.
Figures
References
-
-
For arylation of heterocycles see: Nakamura N, Tajima Y, Sakai K. Heterocycles. 1982;17:235.Akita Y, Ohta A. Heterocycles. 1982;19:329.Pivsa-Art S, Satoh T, Kawamura Y, Miura M, Nomura M. Bull Chem Soc Jpn. 1998;71:467.Park CH, Ryabova V, Seregin IV, Sromek AW, Gevorgyan V. Org Lett. 2004;6:1159.Touré BB, Lane BS, Sames D. Org Lett. 2006;8:1979.Seregin IV, Gevorgyan V. Chem Soc Rev. 2007;36:1173.
-
-
-
For pioneering work on Pd(0)-catalyzed arylation of arenes see: Hennings DD, Iwasa S, Rawal VH. J Org Chem. 1997;62:2.Satoh T, Kawamura Y, Miura M, Nomura M. Angew Chem Int Ed. 1997;36:1740.
-
-
-
For Pd(0)-catalyzed intermolecular arylation of sp2 C–H bonds see: Kametani Y, Satoh T, Miura M, Nomura M. Tetrahedron Lett. 2000;41:2655.Lafrance M, Fagnou K. J Am Chem Soc. 2006;128:16496.Chiong HA, Pham QN, Daugulis O. J Am Chem Soc. 2007;129:9879.
-
-
- Dyker G. Angew Chem Int Ed. 1992;31:1023.
- Baudoin O, Herrbach A, Guéritte F. Angew Chem Int Ed. 2003;42:5736. - PubMed
- Zhao J, Campo M, Larock RC. Angew Chem Int Ed. 2005;44:1873. - PubMed
- Barder TE, Walker SD, Martinelli JR, Buchwald SL. J Am Chem Soc. 2005;127:4685. - PubMed
- Ren H, Knochel P. Angew Chem Int Ed. 2006;45:3462. - PubMed
- Lafrance M, Gorelsky SI, Fagnou K. J Am Chem Soc. 2007;129:14570. - PubMed
- Watanabe T, Oishi S, Fujii N, Ohno H. Org Lett. 2008;10:1759. - PubMed
-
-
For an example of Cu(II)-catalyzed arylation of sp3 C–H bonds adjacent to a nitrogen atom with boronic acids see: Baslé O, Li CJ. Org Lett. 2008;10:3661.
-
Publication types
MeSH terms
Substances
Grants and funding
LinkOut - more resources
Full Text Sources
Other Literature Sources
Research Materials
