87241-52-9Relevant articles and documents
Reduction of sulfonates and aromatic compounds with the NiCl2 · 2H2O- Li-arene (cat.) combination
Radivoy, Gabriel,Alonso, Francisco,Yus, Miguel
, p. 14479 - 14490 (1999)
A series of alkyl mesylates, dimesylates and alkyl or aryl triflates have been reduced to the corresponding hydrocarbons with nickel(II) chloride dihydrate, an excess of lithium powder and a catalytic amount of DTBB (10 mol%) in THF at room temperature. This methodology applied to enol triflates allowed the preparation of olefins or alkanes depending on the amount of the Ni(II) salt used. The reduction of different aromatic or heteroaromatic compounds under the above mentioned conditions leads to the partial or total reduction of the starting materials, the process being a reasonable alternative to the well-known Birch reaction. The use of the deuterium oxide- containing nickel(lI) salt allows the simple preparation of deuterated products.
Nickel-Catalyzed Cyanation of Aryl Chlorides and Triflates Using Butyronitrile: Merging Retro-hydrocyanation with Cross-Coupling
Yu, Peng,Morandi, Bill
supporting information, p. 15693 - 15697 (2017/12/02)
We describe a nickel-catalyzed cyanation reaction of aryl (pseudo)halides that employs butyronitrile as a cyanating reagent instead of highly toxic cyanide salts. A dual catalytic cycle merging retro-hydrocyanation and cross-coupling enables the conversion of a broad array of aryl chlorides and aryl/vinyl triflates into their corresponding nitriles. This new reaction provides a strategically distinct approach to the safe preparation of aryl cyanides, which are essential compounds in agrochemistry and medicinal chemistry.
