Journal article
Enolonium Species-Umpoled Enolates
Enolonium species/iodo(III) enolates of carbonyl compounds have been suggested to be intermediates in a wide variety of hypervalent iodine induced chemical transformations of ketones, including α-C-O, α-C-N, α-C-C, and alpha-carbon- halide bond formation, but they have never been characterized. We report that these elusive umpoled enolates may be made as discrete species that are stable for several minutes at-78 degrees C, and report the first spectroscopic identification of such species.
It is shown that enolonium species are direct intermediates in C-O, C-N, C-Cl, and C-C bond forming reactions. Our results open up chemical space for designing a variety of new transformations. We showcase the ability of enolonium species to react with prenyl, crotyl, cinnamyl, and allyl silanes with absolute regioselectivity in up to 92% yield.
Language: | English |
---|---|
Year: | 2017 |
Pages: | 2599-2603 |
ISSN: | 15213773 and 14337851 |
Types: | Journal article |
DOI: | 10.1002/anie.201610274 |
ORCIDs: | 0000-0001-9774-2358 , 0000-0001-7175-3796 and 0000-0001-7790-4129 |