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

Gangwei Wang; John Bower

doi:10.1021/jacs.7b13087

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

Gangwei Wang, John Bower

School of Chemistry

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Abstract

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.

Original language	English
Pages (from-to)	2743-2747
Number of pages	5
Journal	Journal of the American Chemical Society
Volume	140
Issue number	8
Early online date	20 Feb 2018
DOIs	https://doi.org/10.1021/jacs.7b13087
Publication status	Published - 28 Feb 2018

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title = "Modular Access to Azepines by Directed Carbonylative C-C Bond Activation of Aminocyclopropanes",

abstract = "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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AU - Wang, Gangwei

AU - Bower, John

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N2 - 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.

AB - 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.

U2 - 10.1021/jacs.7b13087

DO - 10.1021/jacs.7b13087

M3 - Article (Academic Journal)

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 8

ER -

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

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