Modular Access to Azepines by Directed Carbonylative C–C Bond Activation of Aminocyclopropanes

A modular Rh-catalyzed entry to azepines is outlined. Under a CO atmosphere, protecting group directed C–C bond activation of aminocyclo­propanes provides rhodacyclo­pentanones. These intermediates are effective for intramolecular C–H metalation of either an N-aryl or N-vinyl unit en route to azepin...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 140; no. 8; pp. 2743 - 2747
Main Authors Wang, Gang-Wei, Bower, John F
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 28.02.2018
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Communication
Physical Sciences
Science & Technology
RHODACYCLOPENTANONES
COMPLEXES
AMINO-SUBSTITUTED CYCLOPROPANES
CARBON-CARBON
3+1+2 CYCLOADDITIONS
REDUCTIVE ELIMINATION
DERIVATIVES
CYCLOBUTANONES
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Summary:A modular Rh-catalyzed entry to azepines is outlined. Under a CO atmosphere, protecting group directed C–C bond activation of aminocyclo­propanes provides rhodacyclo­pentanones. These intermediates are effective for intramolecular C–H metalation of either an N-aryl or N-vinyl unit en route to azepine ring systems. Thus, byproduct-free heterocyclizations are enabled by sequential C–C activation and C–H functionalization steps.
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content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.7b13087