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Aryl Nitriles From Alkynes Using Tert-Butyl Nitrite: Metal-Free Approach To C≡C Bond Cleavage.
U. Dutta, D. Lupton, D. Maiti
Published 2016 · Chemistry, Medicine
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Alkyne C≡C bond breaking, outside of alkyne metathesis, remains an underdeveloped area in reaction discovery. Recently, nitrogenation has been reported to allow nitrile formation from alkynes. A new protocol for the metal-free C≡C bond cleavage of terminal alkynes to produce nitriles is reported. This method provides an opportunity to synthesize a vast range of nitriles containing aryl, heteroaryl, and natural product derivatives (38 examples). In addition, the potential of (t)BuONO to act as a powerful nitrogenating agent for terminal aryl alkynes is demonstrated.
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