Aryl nitriles from alkynes using tert-butyl nitrite: metal-free approach to C≡C bond cleavage

Uttam Dutta, David W. Lupton, Debabrata Maiti

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70 Citations (Scopus)


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 tBuONO to act as a powerful nitrogenating agent for terminal aryl alkynes is demonstrated. 

Original languageEnglish
Pages (from-to)860-863
Number of pages4
JournalOrganic Letters
Issue number4
Publication statusPublished - 19 Feb 2016

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