1333245-00-3Relevant articles and documents
Copper-mediated cyanation of aryl halide with the combined cyanide source
Zhang, Guoying,Ren, Xinyi,Chen, Jianbin,Hu, Maolin,Cheng, Jiang
, p. 5004 - 5007 (2011)
A simple copper-mediated cyanation of aryl halide with the combination of ammonium bicarbonate and N,N-dimethylformamide as a cyanide source is achieved, providing nitriles in moderate to good yields. This new approach represents an exceedingly practical and safe method for the synthesis of aryl nitriles.
Late-Stage Carbon Isotope Exchange of Aryl Nitriles through Ni-Catalyzed C-CN Bond Activation
Reilly, Sean W.,Lam, Yu-Hong,Ren, Sumei,Strotman, Neil A.
, p. 4817 - 4823 (2021)
A facile one-pot strategy for 13CN and 14CN exchange with aryl, heteroaryl, and alkenyl nitriles using a Ni phosphine catalyst and BPh3 is described. This late-stage carbon isotope exchange (CIE) strategy employs labeled Zn(CN)2 to facilitate enrichment using the nonlabeled parent compound as the starting material, eliminating de novo synthesis for precursor development. A broad substrate scope encompassing multiple pharmaceuticals is disclosed, including the preparation of [14C] belzutifan to illustrate the exceptional functional group tolerance and utility of this labeling approach. Preliminary experimental and computational studies suggest the Lewis acid BPh3 is not critical for the oxidative addition step and instead plays a role in facilitating CN exchange on Ni. This CIE method dramatically reduces the synthetic steps and radioactive waste involved in preparation of 14C labeled tracers for clinical development.
Nickel-catalyzed decarbonylative alkylidenation of phthalimides with trimethylsilyl-substituted alkynes
Shiba, Takahiro,Kurahashi, Takuya,Matsubara, Seijiro
supporting information, p. 13636 - 13639 (2013/10/01)
We have developed a nickel-catalyzed transformation, in which phthalimides react with trimethylsilyl-substituted alkynes in the presence of Ni(0)/PMe 3/MAD catalyst to provide isoindolinones. The reaction process displays an unusual mechanistic