Cycloadditions to Epoxides Catalyzed by GroupIII-V Transition-Metal Complexes

Citation data:

ChemCatChem, ISSN: 1867-3899, Vol: 7, Issue: 13, Page: 1906-1917

Publication Year:
2015
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Citations 46
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Repository URL:
http://hdl.handle.net/10754/566092
DOI:
10.1002/cctc.201500231
Author(s):
Valerio D'Elia; Jérémie D. A. Pelletier; Jean-Marie Basset
Publisher(s):
Wiley; Wiley-Blackwell; Wiley-VCH Verlag
Tags:
Chemical Engineering; Chemistry; Cycloaddition; Epoxides; Reaction mechanisms; Synthetic methods; Transition metals
article description
Complexes of groupIII-V transition metals are gaining increasing importance as Lewis acid catalysts for the cycloaddition of dipolarophiles to epoxides. This review examines the latest reports, including homogeneous and heterogeneous applications. The pivotal step for the cycloaddition reactions is the ring opening of the epoxide following activation by the Lewis acid. Two modes of cleavage (Cidentified depending primarily on the substitution pattern of the epoxide, with lesser influence observed from the Lewis acid employed. The widely studied cycloaddition of CO2 to epoxides to afford cyclic carbonates (CO bond cleavage) has been scrutinized in terms of catalytic efficiency and reaction mechanism, showing that unsophisticated complexes of groupIII-V transition metals are excellent molecular catalysts. These metals have been incorporated, as well, in highly performing, recyclable heterogeneous catalysts. Cycloadditions to epoxides with other dipolarophiles (alkynes, imines, indoles) have been conducted with scandium triflate with remarkable performances (CC bond cleavage).