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Nickel‐Catalyzed Synthesis of <i>N</i>‐Aryl‐1,2‐dihydropyridines by [2+2+2] Cycloaddition of Imines with Alkynes through T‐Shaped 14‐Electron Aza‐Nickelacycle Key Intermediates
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Description
<jats:title>Abstract</jats:title><jats:p>Despite there being a straightforward approach for the synthesis of 1,2‐dihydropyridines, the transition‐metal‐catalyzed [2+2+2] cycloaddition reaction of imines with alkynes has been achieved only with imines containing an <jats:italic>N</jats:italic>‐sulfonyl or ‐pyridyl group. Considering the importance of 1,2‐dihydropyridines as useful intermediates in the preparation of a wide range of valuable organic molecules, it would be very worthwhile to provide novel strategies to expand the scope of imines. Herein we report a successful expansion of the scope of imines in nickel‐catalyzed [2+2+2] cycloaddition reactions with alkynes. In the presence of a nickel(0)/PCy<jats:sub>3</jats:sub> catalyst, a reaction with <jats:italic>N</jats:italic>‐benzylidene‐<jats:italic>P,P</jats:italic>‐diphenylphosphinic amide was developed. Moreover, an application of <jats:italic>N</jats:italic>‐aryl imines to the reaction was also achieved by adopting N‐heterocyclic carbene ligands. The isolation of an (η<jats:sup>2</jats:sup>‐<jats:italic>N</jats:italic>‐aryl imine)nickel(0) complex containing a 14‐electron nickel(0) center and a T‐shaped 14‐electron five‐membered aza‐nickelacycle is shown. These would be considered as key intermediates of the reaction. The structure of these complexes was unambiguously determined by NMR spectroscopy and X‐ray analyses.</jats:p>
Journal
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- Chemistry – A European Journal
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Chemistry – A European Journal 20 (14), 4105-4110, 2014-02-27
Wiley
