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After the first structural characterization of the N-heterocyclic carbene (NHC) by Arduengo and co-workers in 1991, NHCs have been widely used to stabilize a whole variety of unstable complexes of main-group and transition elements in lower oxidation state. Recently, another class of stable cyclic carbenes, namely, cyclic (alkyl)(amino)carbenes (cAACs) reported by Bertrand et al. in 2005, have received much attention due to better σ-donating as well as more π-accepting properties than NHCs.
1 As a result, various unusual diamagnetic and paramagnetic main group species which were difficult or impossible to achieve by conventional methods were successfully stabilized by employing cAACs.
2 For example, a versatile reagent [lithium
phosphinidene; {cAACPLi(THF)2}2] for introducing phosphorus atoms into organic and
inorganic substrates was stabilized by cAAC.3 Various cAAC assisted organosilicon radicals and
neutral radicals of aluminium were isolated from commodity precursors.
4 Finally, the use of
organostannoxane platforms for supramolecular assemblies and single source precursors for
binary oxide will be presented.5
References:
(1) Melaimi, M.; Jazzar, R.; Soleilhavoup, M.; Bertrand, G. Angew.Chem. Int. Ed. 2017, 56, 10046 –10068
(2) Kundu, S.; Li, B.; Kretsch, J.; Herbst-Irmer, R.; Andrada, D. M.; Frenking, G.; Stalke, D.; Roesky, H. W.
Angew. Chem. Int. Ed. 2017, 56, 4219–4223.
(3) (a) Kundu, S.; Sinhababu, S.; Luebben, A. V.; Mondal, T.; Koley, D.; Dittrich, B.; Roesky, H. W. J. Am. Chem.
Soc. 2018, 140, 151‒154. (b) Kundu, S.; Sinhababu, S.; Siddiqui, M. M.; Luebben, A. V.; Dittrich, B.; Yang, T.;
Frenking, G.; Roesky, H. W. J. Am. Chem. Soc. DOI: 10.1021/jacs.8b06230
(4) Kundu, S.; Samuel, P. P.; Sinhababu, S.; Luebben, A. V.; Dittrich, B.; Andrada, D. M.; Frenking, G.; Stückl, A.
C.; Schwederski, B.; Paretzki, A.; Kaim, W.; Roesky, H. W. J. Am. Chem. Soc. 2017, 139, 11028–11031.
(5) Kundu, S.; Chakraborty, A.; Mondal, K.; Chandrasekhar, V. Cryst. Growth Des. 2014, 14, 861–870. |