Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 43, Pages 15324-15327Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b10240
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Funding
- EPSRC [EP/I038071/1]
- EPSRC Bristol Chemical Synthesis Doctoral Training Centre [EP/L015366/1]
- University of Bristol
- Xunta de Galicia
- Ramon Areces Foundation
- Deutsche Forschungsgemeinschaft [SFB 749]
- ERC [670668]
- Engineering and Physical Sciences Research Council [EP/I038071/1, EP/K03927X/1] Funding Source: researchfish
- EPSRC [EP/I038071/1, EP/L015366/1, EP/K03927X/1] Funding Source: UKRI
- European Research Council (ERC) [670668] Funding Source: European Research Council (ERC)
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Allylboronic esters react readily with carbonyls and imines (pi-electrophiles), but are unreactive toward a range of other electrophiles. By addition of an aryllithium, the corresponding allylboronate complexes display enhanced nucleophilicity, enabling addition to a range of electrophiles (tropylium, benzodithiolylium, activated pyridines, Eschenmoser's salt, Togni's reagent, Selectfluor, diisopropyl azodicarboxylate (DIAD), MeSX) in high regio- and stereocontrol. This protocol provides access to key new functionalities, including quaternary stereogenic centers bearing moieties such as fluorine and the trifluoromethyl group. The allylboronate complexes were determined to be 7 to 10 orders o f magnitude more reactive than the parent boronic ester.
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