Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 359, Issue 4, Pages 623-628Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201600813
Keywords
allylic compounds; amination; C-H activation; homogeneous catalysis; palladium
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Funding
- Universita degli Studi dell'Insubria
- CNRS
- UPMC
- Labex Michem
- CMST COST Action [CA15106, CM1205]
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A study of the palladium(II)-catalyzed cyclization of unsaturated N-sulfonylamides was undertaken, using (diacyloxyiodo)benzenes as terminal oxidizing agents. Different reactivities were observed as a function of the nature of the unsaturation (terminal vs. internal), or of the hypervalent iodine compound used (diacetoxyiodobenzene vs. bistrifluoroacetoxyiodobenzene). Proper parameter selection allows the direction of the cyclization to be chosen towards either a global aminoacetoxylation, an allylic amination via aminopalladation, or an allylic amination via allylic C-H activation.
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