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Synthesis of Nitrogen Heterocycles via Directed Carbonylative C–C Bond Activation of Cyclopropanes

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This review concentrates on recent developments from our laboratory concerning the Rh-catalyzed carbonylative C–C bond activation of cyclopropanes. Specifically, we have found that N-based directing groups are effective at controlling the regioselectivity of C–C bond activation during the formation of rhodacyclopentanone intermediates. These engage tethered π-unsaturated components (e.g. alkenes) or conventional nucleophiles in cycloaddition and heterocyclization processes, respectively. Using this approach, direct and modular access to a wide range of complex heterocyclic ring systems is achieved. The review summarizes the scope of our methodologies and outlines key mechanistic features.
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Keywords: CARBONYLATION; CYCLOADDITION; CYCLOPROPANE; C–C BOND ACTIVATION; RHODIUM

Document Type: Research Article

Affiliations: 1: School of Chemistry, University of Bristol Bristol, BS8 1TS, United Kingdom 2: School of Chemistry, University of Bristol Bristol, BS8 1TS, United Kingdom;, Email: [email protected]

Publication date: 01 September 2018

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  • International Journal for Chemistry and Official Membership Journal of the Swiss Chemical Society (SCS) and its Divisions

    CHIMIA, a scientific journal for chemistry in the broadest sense, is published 10 times a year and covers the interests of a wide and diverse readership. Contributions from all fields of chemistry and related areas are considered for publication in the form of Review Articles and Notes. A characteristic feature of CHIMIA are the thematic issues, each devoted to an area of great current significance.

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