Cyclic Alkyl Amino Carbene (CAAC) Precursor

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CAACs (Cyclic Alkyl Amino Carbenes) have been developed by the Bertrand group as an alternative cyclic carbene species to that of of NHCs (N-Heterocyclic carbenes).¹⁾ CAACs are analogs of NHCs in which the one of the key nitrogens has been replaced with an electron-rich carbon atom. As a result, the CAACs' carbene carbon behaves as a strong σ donnor.²⁾ CAACs are able to coordinate to not only transition metals but also non-transition metals and boron. The unique reactivity of those complexes have been reported in recent years and is an area of active research.^3-10)

CAAC

Product

D5596: 2-(2,6-Diisopropylphenyl)-3,3-dimethyl-2-azaspiro[4.5]dec-1-en-2-ium Hydrogen Dichloride

References

1)Stable Cyclic (Alkyl)(amino)carbenes as Rigid or Flexible, Bulky, Electron-Rich Ligands for Transition-Metal Catalysts: A Quaternary Carbon Atom Makes the Difference V.
- Lavallo, Y. Canac, C. Präsang, B. Donnadieu, G. Bertrand, Angew. Chem. Int. Ed. 2005, 44, 5705.
2)Cyclic (alkyl)(amino)carbene Gold(I) Complexes: A Synthetic and Structural Investigation
- G. D. Frey, R. D. Dewhurst, S. Kousar, B. Donnadieu, G. Bertrand, J. Organomet. Chem. 2008, 693, 1674.
3)Cyclic (Alkyl)(amino)carbenes (CAACs): Stable Carbenes on the Rise
- M. Soleilhavoup, G. Bertrand, Acc. Chem. Res. 2015, 48, 256.
4)Group 1 and 2 Cyclic (alkyl)(amino)carbene Complexes
- Z. R. Turner, J. Buffet, Dalton Trans. 2015, 44, 12985.
5)Synthesis and Characterization of a Neutral Tricoordinate Organoboron Isoelectronic with Amines
- R. Kinjo, B. Donnadieu, M. A. Celik, G. Frenking, G. Bertrand, Science 2011, 333, 610.
6)Building a Lewis Base with Boron
- Y. Wang, G. H. Robinson, Science 2011, 333, 530.
7)Nitrogen fixation and reduction at boron
- M. Légaré, G. Bélanger-Chabot, R. D. Dewhurst, E. Welz, I. Krummenacher, B. Engels, H. Braunschweig, Science 2018, 359, 896.
8)Hydrogenation of fluoroarenes: Direct access to all-cis-(multi)fluorinated cycloalkanes
- M. P. Wiesenfeldt, Z. Nairoukh, W. Li, F. Glorius, Science 2017, 357, 908.
9)Highly Selective Hydrogenation of Aromatic Ketones and Phenols Enabled by Cyclic (Amino)(alkyl)carbene Rhodium Complexes
- Y. Wei, B. Rao, X. Cong, X. Zeng, J. Am. Chem. Soc. 2015, 137, 9250.
10)Cyclic Alkyl Amino Carbene (CAAC) Ruthenium Complexes as Remarkably Active Catalysts for Ethenolysis
- V. M. Marx, A. H. Sullivan, M. Melaimi, S. C. Virgil, B. K. Keitz, D. S. Weinberger, G. Bertrand, R. H. Grubbs, Angew. Chem. Int. Ed. 2015, 54, 1919.

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CAAC (Cyclic Alkyl Amino Carbene) Precursor (PDF file)

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Carbon-Donor Ligands

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