Projects per year
Abstract
In the presence of trifluoromethylsulfonium reagents, boronate complexes derived from 2-lithio furan and non-racemic secondary and tertiary alkyl or aryl boronic esters undergo deborylative three-component coupling to give the corresponding 2,5-disubstituted furans with excellent levels of enantiospecificity. The process proceeds via the reaction of boronate complexes with a trifluoromethyl radical, which triggers 1,2-metallate rearrangement upon single-electron oxidation. Alternative electrophiles can also be used in place of trifluoromethylsulfonium reagents to effect similar three-component coupling reactions.
Original language | English |
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Pages (from-to) | 1810-1814 |
Number of pages | 5 |
Journal | Angewandte Chemie - International Edition |
Volume | 56 |
Issue number | 7 |
Early online date | 30 Jan 2017 |
DOIs | |
Publication status | Published - 6 Feb 2017 |
Keywords
- boronic esters
- cross-coupling
- furans
- stereospecificity
- trifluoromethylation
Fingerprint Dive into the research topics of 'Enantiospecific Trifluoromethyl-Radical-Induced Three-Component Coupling of Boronic Esters with Furans'. Together they form a unique fingerprint.
Projects
- 3 Finished
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Changing the Synthesis Landscape with Boron at the Helm: from Chiral Organometallics to Assembly Line Synthesis
14/05/12 → 13/01/18
Project: Research