72335-57-0Relevant academic research and scientific papers
Organometallic Lewis Acids, Part LXII. Chiral Carbonyl-Cyclopentadienyl-Triphenylphosphine-Iron and -Ruthenium Complexes with Tertiary Nitriles [CpM(CO)(PPh3)(N≡C–CR1R2R3)]+ BF4–
Missling, Christopher U.,Sünkel, Karlheinz,Langhals, Heinz,Beck, Wolfgang
, p. 1262 - 1268 (2017/11/10)
A series of tertiary nitriles was synthesized by alkylation of acetonitrile, primary and secondary nitriles, using alkylbromides and sodium amide in liquid ammonia. By reaction of the in situ formed organometallic Lewis acids [CpM(CO)(PPh3)]su
Arylthio-metal exchange of α-arylthioalkanenitriles
Nath, Dinesh,Skilbeck, Melanie C.,Coldham, Iain,Fleming, Fraser F.
supporting information, p. 62 - 65 (2014/01/23)
The addition of BuLi, Bu3MgLi, Et2ZnBuLi, or Me 2CuLi to α-arylthioalkanenitriles triggers an arylthio-metal exchange. NMR spectroscopic analyses implicate organometallic attack on sulfur forming a three-coordinate sulfidate as the key intermediate. Electrophilic trapping affords tertiary and quaternary nitriles in high yield. The method addresses the challenge of improving the functional group tolerance and preventing polyalkylations.
Sulfinylnitriles: Sulfinyl-metal exchange-alkylation strategies
Nath, Dinesh,Fleming, Fraser F.
supporting information, p. 2023 - 2029 (2013/03/14)
Adding organolithiums, Grignard reagents, or zincates to sulfinylnitriles triggers a facile sulfinyl-metal exchange to afford N- or C-metalated nitriles. Sulfinyl-magnesium exchange-alkylations efficiently install quaternary and tertiary centers, even in
