57775-05-0Relevant articles and documents
Copper-catalyzed benzylic C-H oxygenation under an oxygen atmosphere via N-H imines as an intramolecular directing group
Zhang, Line,Ang, Gim Yean,Chiba, Shunsuke
supporting information; experimental part, p. 1622 - 1625 (2011/05/05)
Copper-catalyzed benzylic C-H oxygenation under an oxygen atmosphere was developed starting from carbonitriles and Grignard reagents via N-H imine intermediates. The present process is characterized by the following two-step sequence in a one-pot manner: (1) addition of Grignard reagents to carbonitriles to form N-H imines and (2) benzylic C-H oxygenation (C=O bond formation) triggered by 1,5-hydrogen atom transfer with transient iminyl copper species.
Tetraphosphine/palladium catalysed Suzuki cross-coupling reactions of aryl halides with alkylboronic acids
Kondolff, Isabelle,Doucet, Henri,Santelli, Maurice
, p. 3813 - 3818 (2007/10/03)
Through the use of [PdCl(C3H5)]2/cis,cis, cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane as a catalyst, a range of aryl bromides and chlorides undergoes Suzuki cross-coupling with alkylboronic acids in good yields. Several alkyl substituents such as ethyl, n-butyl, n-octyl, isobutyl or 2,2-dimethylpropyl on the alkylboronic acids have been successfully used. The functional group tolerance on the aryl halide is remarkable; substituents such as fluoro, methyl, methoxy, acetyl, formyl, benzoyl, nitro or nitrile are tolerated. Furthermore, this catalyst can be used at low loading, even for reactions of sterically hindered aryl bromides.
Reductive activation of arenes. XII. Reaction of the product of phthalonitrile one-electron reduction with butyl halides in liquid ammonia
Panteleeva,Bilkis,Steingarts
, p. 1632 - 1639 (2007/10/03)
The product of one-electron reduction of the phthalonitrile with metallic potassium in liquid ammonia reacts with butyl halides (BuCl, BuBr, BuI, s-BuBr, t-BuBr, t-BuI) to yield compounds of alkyl bonding in ipso(2-butylbenzonitriles) and unsubstituted (4-butyl-1,2-dicyanobenzenes and 2,5-dibutylbenzonitriles) positions of the aromatic ring of the original dinitrile. The dependence of the product composition on the character of alkyl moiety and halogen atom in the butyl halide is rationalized by reaction mechanism including at the first stage electron transfer from the anion-radical of the phthalonitrile to the alkyl halide and followed by recombination of the alkyl radical produced with another molecule of anionradical.