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Interrupted SNAr-Alkylation Dearomatization
Altundas, Bilal Marrazzo, John-Paul R. Brinck, Tore Absil, Christopher Fleming, Fraser F.
Altundas, Bilal
Marrazzo, John-Paul R.
Brinck, Tore
Absil, Christopher
Fleming, Fraser F.
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Journal article
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2024-02-19
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Chemistry
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https://doi.org/10.1021/jacsau.3c00813
Abstract
Dearomatizations provide powerful synthetic routes to rapidly assemble substituted carbocycles and heterocycles found in a plethora of bioactive molecules. Harnessing the advantages of dearomatization typically requires vigorous reagents because of the difficulty in disrupting the stable aromatic core. A relatively mild dearomatization strategy is described that employs lithiated nitriles or isocyanides in a simple SNAr-type addition to form σ-complexes that are trapped by alkylation. The dearomatizations are diastereoselective and efficient and rapidly install two new carbon–carbon bonds, one of which is a quaternary center, as well as nitrile, isocyanide, and cyclohexadiene functionalities.
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American Chemical Society (ACS)
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JACS Au, Vol. 4, Iss. 3
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Attribution-NonCommercial-NoDerivs CC BY-NC-ND