title: Aryl Nitriles from Alkynes Using tert-Butyl Nitrite: Metal-Free Approach to C≡C Bond Cleavage.
abstract: 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.
authors: Department of Chemistry, Indian Institute of Technology Bombay , Powai, Mumbai-400 076, India.|IITB-Monash Research Academy, IIT Bombay , Powai, Mumbai-400076, India.
authors: Uttam
authors: U
authors: Dutta
authors: IITB-Monash Research Academy, IIT Bombay , Powai, Mumbai-400076, India.|School of Chemistry, Monash University , Clayton 3800, Victoria, Australia.
authors: David W
authors: DW
authors: Lupton
authors: Department of Chemistry, Indian Institute of Technology Bombay , Powai, Mumbai-400 076, India.|IITB-Monash Research Academy, IIT Bombay , Powai, Mumbai-400076, India.
authors: Debabrata
authors: D
authors: Maiti