- Generality
- Reagent Availability
- Experimental User Friendliness
- Future Potential
- Criteria #5
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General Characteristics
The direct coupling between unsubstituted aromatic rings and olefins in the presence of palladium catalysts is called the Fujiwara-Moritani reaction. This reaction is one of the early examples of transition metal-promoted C-H activation reactions.
In terms of chemical transformation, this reaction corresponds formally to the oxidative Mizoroki-Heck reaction.
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General References
- Moritani, I.; Fujiwara, Y. Tetrahedron Lett. 1967, 8, 1119. doi:10.1016/S0040-4039(00)90648-8
- Fujiwara, Y.; Moritani, I.; Matsuda, M.; Teranishi, S. Tetrahedron Lett. 1968, 9, 633. doi:10.1016/S0040-4039(01)98820-3
- Fujiwara, Y.; Moritani, I.; Danno, S.; Asano, R.; Teranishi, S. J. Am. Chem. Soc. 1969, 91, 7166. DOI: 10.1021/ja01053a047
- Fujiwara, Y.; Aasano, R.; Moritani, i.; Teranishi, S. J. Org. Chem. 1976, 41, 1681. DOI: 10.1021/jo00872a002
- Yokota, T.; Tani, M.; Sakaguchi, S.; Ishii, Y. J. Am. Chem. Soc. 2003, 125, 1476. DOI: 10.1021/ja028903a
- Nishikata, T.; Lipshutz, B. H. Org. Lett. 2010, 12, 1972. DOI: 10.1021/ol100331h
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Reaction Mechanism
Ref: J. Am. Chem. Soc. 2005, 127, 13754.
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Examples
Modifications and applications of the Fujiwara-Moritani reaction have been studied actively in recent years, especially using substrates containing directing groups. A number of highly regioselective systems have been reported, which was difficult under the original conditions.
Jin-Quan Yu developed an efficient carboxylic acid-directed catalytic system[1] and used it elegantly in the convergent total synthesis of (+)-lithospermic acid.[2]
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Experimental Procedure
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Experimental Tips
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References
[1](a) Wang, D.-H.; Engle, K. M.; Shi, B.-F.; Yu, J.-Q. Science 2010, 327, 315. DOI: 10.1126/science.1182512 (b) Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2010, 49, 6169. DOI: 10.1002/anie.201002077 (c) Engle, K. M.; Wang, D.-H.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 14137. DOI: 10.1021/ja105044s
[2] Wang, D.-H.; Yu, J.-Q. J. Am. Chem. Soc. 2011, 133, 5767. doi:10.1021/ja2010225
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Related Reactions
- Cross Dehydrogenative Coupling (CDC)
- Catalytic C-H Oxidation
- Catalytic C-H activation
- Mizoroki-Heck Reaction
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Related Books
[amazonjs asin=”0470033940″ locale=”US” title=”The Mizoroki-Heck Reaction”]
[amazonjs asin=”3642123554″ locale=”US” title=”C-H Activation (Topics in Current Chemistry)”]
[amazonjs asin=”3527310746″ locale=”US” title=”Handbook of C-H Transformations”]
[amazonjs asin=”3642084362″ locale=”US” title=”Activation of Unreactive Bonds and Organic Synthesis (Topics in Organometallic Chemistry)”]
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External Links