Metal carbenes or carbenoid complexes are one of the versatile intermediates in organic
synthesis.1 Transition metal-catalyzed transformation of metal carbenes have been
extensively used for the synthesis of the biologically valuable heterocycles.2 Although free
carbenes would be considered to be highly reactive intermediates, metal-ligated analogues
can be generated under very mild conditions and thus impressive selectivities can be obtained
in subsequent reactions. These intermediates are capable of undergoing a range of
unconventional reactions depending on various functional groups.3 Due to their high
reactivity, they initiate cascade sequences which leads to the generation of complex structural
molecules. The most usual method of generating a metal carbene intermediate is the carbene
transfer from an organic diazo compound to a suitable metal catalyst, but number of other
precursors are available for in-situ generation of metal carbenes. In this seminar, generation
of metal carbenes from various precursors and their transformations will be discussed.
Reference:
[1] (a) Davies, H. M. L.; Denton, J. R. Chem. Soc. Rev. 2009, 38, 3061. (b) Padwa, A. Chem. Soc. Rev. 2009,
38, 3072. (c) Zhang, Z.; Wang, J. Tetrahedron 2008, 64, 6577.
[2] Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo
Compounds: From Cyclopropanes To Ylides; Wiley: New York, 1998.
[3] Ma, S.; Jia, M. Angew. Chem. Int. Ed. 2016, 55, 9134.