TY - JOUR
T1 - Aryl nitriles from alkynes using tert-butyl nitrite
T2 - metal-free approach to C≡C bond cleavage
AU - Dutta, Uttam
AU - Lupton, David W.
AU - Maiti, Debabrata
PY - 2016/2/19
Y1 - 2016/2/19
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=84958964566&partnerID=8YFLogxK
UR - http://pubs.acs.org/doi/pdf/10.1021/acs.orglett.6b00147
U2 - 10.1021/acs.orglett.6b00147
DO - 10.1021/acs.orglett.6b00147
M3 - Article
AN - SCOPUS:84958964566
VL - 18
SP - 860
EP - 863
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 4
ER -