Abstract
A formal CH2−CH2 homologation conducted with C1 carbenoids on a carbon electrophile for the obtainment of a four-membered cycle is reported. The logic proposes the consecutive delivery of two single nucleophilic CH2 units to an isothiocyanate—as competent electrophilic partner—resulting in the assembling of a rare imino-thietane cluster. The single synthetic operation procedure documents genuine chemocontrol, as indicated by the tolerance to various reactive elements decorating the starting materials. Significantly, the double homologation protocol is accomplished directly on a carbon electrophile, thus not requiring the installation of heteroatom-centered manifolds (e.g. boron).
Original language | English |
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Pages (from-to) | 24854-24858 |
Number of pages | 5 |
Journal | Angewandte Chemie - International Edition |
Volume | 60 |
Issue number | 47 |
DOIs | |
Publication status | Published - 15 Nov 2021 |
Austrian Fields of Science 2012
- 104015 Organic chemistry
Keywords
- carbenoids
- chemoselectivity
- homologation
- isothiocyanates
- thietanes