Journal
CHEMICAL SCIENCE
Volume 9, Issue 11, Pages 2873-2878Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8sc00181b
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Funding
- EPSRC [EP/M026221/1]
- Ramsay Memorial Trust
- QMUL
- RSC Research Fund
- Engineering and Physical Sciences Research Council [EP/M026221/1] Funding Source: researchfish
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Transition metal-free intramolecular hydride transfer onto arynes is reported for the first time. This unique transformation is utilized in redox-neutral intermolecular alpha-functionalization reactions of different tertiary amines, generating C(sp(3))-C(sp(3)/sp(2)/sp) bonds in a single synthetic operation. Deuterium labeling studies support initial cleavage of the alpha-C-H bond via intramolecular 1,5-hydride transfer onto the aryne, which leads to activation of a range of integrated pronucleophiles and ultimately affords a new approach to cross-dehydrogenative coupling reactions which utilize aryne intermediates.
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