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Reductive Ring Opening of Arylcyclopropanecarboxamides Accompanied by Borylation and Enolate Formation.

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Treatment of arylcyclopropanecarboxamides with a sodium dispersion in the presence of methoxypinacolborane as a reduction-resistant electrophile leads to reductive cleavage of the cyclopropane ring followed by instant trapping with the… Click to show full abstract

Treatment of arylcyclopropanecarboxamides with a sodium dispersion in the presence of methoxypinacolborane as a reduction-resistant electrophile leads to reductive cleavage of the cyclopropane ring followed by instant trapping with the boron electrophile to yield the enolates of γ-aryl-γ-borylalkanamides. The enolates react further with a different electrophile to yield the corresponding α-substituted amides with anti selectivity.

Keywords: reductive ring; arylcyclopropanecarboxamides accompanied; opening arylcyclopropanecarboxamides; borylation enolate; accompanied borylation; ring opening

Journal Title: Organic letters
Year Published: 2022

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