PalladiumCatalyzed Condensation of NAryl Imines and …ccc.chem.pitt.edu/wipf/Current...
Transcript of PalladiumCatalyzed Condensation of NAryl Imines and …ccc.chem.pitt.edu/wipf/Current...
![Page 1: PalladiumCatalyzed Condensation of NAryl Imines and …ccc.chem.pitt.edu/wipf/Current Literature/Joe_4.pdf · 2014-10-12 · PalladiumCatalyzed Condensation of NAryl Imines and Alkynylbenziodoxolones](https://reader031.fdocuments.in/reader031/viewer/2022013010/5f83e615eee366438a14e396/html5/thumbnails/1.jpg)
Palladium-Catalyzed Condensation
of N-Aryl Imines and Alkynylbenziodoxolones to Form
Multisubstituted Furans
Beili Lu, Junliang Wu, and Naohiko Yoshikai Nanyang Technological University
Singapore J. Am. Chem. Soc. 2014, 136, 11598.
Joseph Salamoun Current Lit. 9/6/14
Wipf Group Joe Salamoun @ Wipf Group Page 1 of 12 10/12/2014
![Page 2: PalladiumCatalyzed Condensation of NAryl Imines and …ccc.chem.pitt.edu/wipf/Current Literature/Joe_4.pdf · 2014-10-12 · PalladiumCatalyzed Condensation of NAryl Imines and Alkynylbenziodoxolones](https://reader031.fdocuments.in/reader031/viewer/2022013010/5f83e615eee366438a14e396/html5/thumbnails/2.jpg)
Selection of Recent Methodologies for the Synthesis of Multisubstituted Furans
Org. Lett. 2013, 15, 5432.
Org. Lett. 2013, 15, 3206.
Chem. Eur. J. 2013, 19, 3584. Joe Salamoun @ Wipf Group Page 2 of 12 10/12/2014
![Page 3: PalladiumCatalyzed Condensation of NAryl Imines and …ccc.chem.pitt.edu/wipf/Current Literature/Joe_4.pdf · 2014-10-12 · PalladiumCatalyzed Condensation of NAryl Imines and Alkynylbenziodoxolones](https://reader031.fdocuments.in/reader031/viewer/2022013010/5f83e615eee366438a14e396/html5/thumbnails/3.jpg)
Selection of Recent Methodologies for the Synthesis of Multisubstituted Furans
Angew. Chem. Int. Ed. 2012, 51, 7562.
J. Am. Chem. Soc. 2012, 134, 19981.
J. Am. Chem. Soc. 2012, 134, 5766.
Angew. Chem. Int. Ed. 2014, 53, 7870.
Joe Salamoun @ Wipf Group Page 3 of 12 10/12/2014
![Page 4: PalladiumCatalyzed Condensation of NAryl Imines and …ccc.chem.pitt.edu/wipf/Current Literature/Joe_4.pdf · 2014-10-12 · PalladiumCatalyzed Condensation of NAryl Imines and Alkynylbenziodoxolones](https://reader031.fdocuments.in/reader031/viewer/2022013010/5f83e615eee366438a14e396/html5/thumbnails/4.jpg)
Previous Work from the Yoshikai Group
J. Am. Chem. Soc. 2012, 134, 9098.
Org. Lett. 2013, 15, 1966.
Org. Lett. 2012, 14, 5488. Joe Salamoun @ Wipf Group Page 4 of 12 10/12/2014
![Page 5: PalladiumCatalyzed Condensation of NAryl Imines and …ccc.chem.pitt.edu/wipf/Current Literature/Joe_4.pdf · 2014-10-12 · PalladiumCatalyzed Condensation of NAryl Imines and Alkynylbenziodoxolones](https://reader031.fdocuments.in/reader031/viewer/2022013010/5f83e615eee366438a14e396/html5/thumbnails/5.jpg)
Pd(II)-Catalyzed Coupling of Imine and Alkynylbenziodoxolone
J. Am. Chem. Soc. 2014, 136, 11598. Joe Salamoun @ Wipf Group Page 5 of 12 10/12/2014
![Page 6: PalladiumCatalyzed Condensation of NAryl Imines and …ccc.chem.pitt.edu/wipf/Current Literature/Joe_4.pdf · 2014-10-12 · PalladiumCatalyzed Condensation of NAryl Imines and Alkynylbenziodoxolones](https://reader031.fdocuments.in/reader031/viewer/2022013010/5f83e615eee366438a14e396/html5/thumbnails/6.jpg)
Initial Result
J. Am. Chem. Soc. 2014, 136, 11598.
x-ray structure of 3aa
Joe Salamoun @ Wipf Group Page 6 of 12 10/12/2014
![Page 7: PalladiumCatalyzed Condensation of NAryl Imines and …ccc.chem.pitt.edu/wipf/Current Literature/Joe_4.pdf · 2014-10-12 · PalladiumCatalyzed Condensation of NAryl Imines and Alkynylbenziodoxolones](https://reader031.fdocuments.in/reader031/viewer/2022013010/5f83e615eee366438a14e396/html5/thumbnails/7.jpg)
Scope of Imines
J. Am. Chem. Soc. 2014, 136, 11598. Joe Salamoun @ Wipf Group Page 7 of 12 10/12/2014
![Page 8: PalladiumCatalyzed Condensation of NAryl Imines and …ccc.chem.pitt.edu/wipf/Current Literature/Joe_4.pdf · 2014-10-12 · PalladiumCatalyzed Condensation of NAryl Imines and Alkynylbenziodoxolones](https://reader031.fdocuments.in/reader031/viewer/2022013010/5f83e615eee366438a14e396/html5/thumbnails/8.jpg)
Scope of EBX
J. Am. Chem. Soc. 2014, 136, 11598. Joe Salamoun @ Wipf Group Page 8 of 12 10/12/2014
![Page 9: PalladiumCatalyzed Condensation of NAryl Imines and …ccc.chem.pitt.edu/wipf/Current Literature/Joe_4.pdf · 2014-10-12 · PalladiumCatalyzed Condensation of NAryl Imines and Alkynylbenziodoxolones](https://reader031.fdocuments.in/reader031/viewer/2022013010/5f83e615eee366438a14e396/html5/thumbnails/9.jpg)
Transformations of Furan 3ca
J. Am. Chem. Soc. 2014, 136, 11598. Joe Salamoun @ Wipf Group Page 9 of 12 10/12/2014
![Page 10: PalladiumCatalyzed Condensation of NAryl Imines and …ccc.chem.pitt.edu/wipf/Current Literature/Joe_4.pdf · 2014-10-12 · PalladiumCatalyzed Condensation of NAryl Imines and Alkynylbenziodoxolones](https://reader031.fdocuments.in/reader031/viewer/2022013010/5f83e615eee366438a14e396/html5/thumbnails/10.jpg)
J. Am. Chem. Soc. 2014, 136, 11598. Joe Salamoun @ Wipf Group Page 10 of 12 10/12/2014
![Page 11: PalladiumCatalyzed Condensation of NAryl Imines and …ccc.chem.pitt.edu/wipf/Current Literature/Joe_4.pdf · 2014-10-12 · PalladiumCatalyzed Condensation of NAryl Imines and Alkynylbenziodoxolones](https://reader031.fdocuments.in/reader031/viewer/2022013010/5f83e615eee366438a14e396/html5/thumbnails/11.jpg)
Three Component Reaction
J. Am. Chem. Soc. 2014, 136, 11598. Joe Salamoun @ Wipf Group Page 11 of 12 10/12/2014
![Page 12: PalladiumCatalyzed Condensation of NAryl Imines and …ccc.chem.pitt.edu/wipf/Current Literature/Joe_4.pdf · 2014-10-12 · PalladiumCatalyzed Condensation of NAryl Imines and Alkynylbenziodoxolones](https://reader031.fdocuments.in/reader031/viewer/2022013010/5f83e615eee366438a14e396/html5/thumbnails/12.jpg)
Conclusions
Valuable addition to the synthesis of multisubstituted furans.
Limited C(2) substitution to iodo-benzene from EBX. But the aryl iodide provides a handle for additional transformations. Three component reaction can address this limitation.
Some limitation to aryl substitutions (vs. alkyl).
Additional mechanistic studies needed.
Joe Salamoun @ Wipf Group Page 12 of 12 10/12/2014