27179-73-3Relevant articles and documents
Suzuki coupling of 2-chloroacrylonitrile, methyl 2-chloroacrylate, or 2-chloroprop-1-en-3-ol with arylboronic acids catalyzed by a palladium-tetraphosphine complex
Berthiol, Florian,Doucet, Henri,Santelli, Maurice
, p. 3019 - 3027 (2006)
The tetraphosphine all-cis-1,2,3,4-tetrakis(diphenylphosphinomethyl) cyclopentane (Tedicyp) in combination with [Pd(C3H 5)Cl]2 affords an efficient catalyst of the coupling of 2-chloroacrylonitrile with arylboronic acids.
Nickel-Catalyzed Cyanation of Aryl Halides and Hydrocyanation of Alkynes via C-CN Bond Cleavage and Cyano Transfer
Chen, Hui,Sun, Shuhao,Liu, Yahu A.,Liao, Xuebin
, p. 1397 - 1405 (2020/02/04)
We report nickel-catalyzed cyanation and hydrocyanation methods to prepare aryl nitriles and vinyl nitriles from aryl halides and alkynes, respectively. Using inexpensive and nontoxic 4-cyanopyridine N-oxide as the cyano shuttle, the methods provide an efficient approach to prepare aryl cyanides and vinyl nitriles under mild and operationally simple reaction conditions with a broad range of functional group tolerances. In hydrocyanation of alkynes, the method demonstrated good regioselectivity, producing predominantly E- or Z-alkenyl nitriles in a controlled manner and exclusively Markovnikov vinyl nitriles when internal diaryl alkynes and terminal alkynes were applied as the substrates, respectively. The preliminary mechanistic investigation indicated that the C-CN bond cleavage process is promoted by oxidative addition to the nickel(I) complex in the cyanation of aryl halides, and further studies via a series of deuterium exchange experiments indicated that water serves as the hydrogen source for the hydrocyanation of alkynes.
Nickel-Catalyzed Highly Regioselective Hydrocyanation of Terminal Alkynes with Zn(CN)2 Using Water as the Hydrogen Source
Zhang, Xingjie,Xie, Xin,Liu, Yuanhong
supporting information, p. 7385 - 7389 (2018/06/11)
The first efficient and general nickel-catalyzed hydrocyanation of terminal alkynes with Zn(CN)2 in the presence of water has been developed. The reaction provides a regioselective protocol for the synthesis of functionalized vinyl nitriles with a range of structural diversity under mild reaction conditions while obviating use of the volatile and hazardous reagent of HCN. Deuterium-labeling experiments confirmed the role of water as the hydrogen source in this hydrocyanation reaction.
