71840-39-6Relevant academic research and scientific papers
B(C6F5)3-Catalyzed Tandem Friedel-Crafts and C?H/C?O Coupling Reactions of Dialkylanilines
Zhai, Gaowen,Liu, Xueting,Ma, Wentao,Wang, Guoqiang,Yang, Liu,Li, Shuhua,Wu, Youting,Hu, Xingbang
supporting information, p. 3082 - 3086 (2020/09/09)
Tandem Friedel-Crafts (FC) and C?H/C?O coupling reactions catalyzed by tris(pentafluorophenyl) borane (B(C6F5)3) were achieved without using any other additive in the absence of solvent. This process can be used for the reactions between a series of dialkylanilines and vinyl ethers with good isolated yields of bis(4-dialkylaminophenyl) compounds. Based on combined theoretical and experimental studies, the possible reaction mechanism was proposed. B(C6F5)3 can activate the C=C and C?O bond for FC and C?H/C?O coupling reactions respectively. The FC reaction is slow, which is followed by a fast C?H/C?O coupling.
Structure and reactivity of boron-ate complexes derived from primary and secondary boronic esters
Feeney, Kathryn,Berionni, Guillaume,Mayr, Herbert,Aggarwal, Varinder K.
supporting information, p. 2614 - 2617 (2015/06/16)
Boron-ate complexes derived from primary and secondary boronic esters and aryllithiums have been isolated, and the kinetics of their reactions with carbenium ions studied. The second-order rate constants have been used to derive nucleophilicity parameters for the boron-ate complexes, revealing that nucleophilicity increased with (i) electron-donating aromatics on boron, (ii) neopentyl glycol over pinacol boronic esters, and (iii) 12-crown-4 ether.
Efficient synthesis of Bis(4-Dimethaminophenyl)arylmethanes and Bis(4-Diamethaminophenyl)alkanes using iodine reagent
Bachhav, Harshal M.,Takale, Balaram S.,Telvekar, Vikas N.
, p. 1909 - 1914 (2013/05/21)
A novel synthetic utility of NaICl2 for the preparation of bis(4-dimethaminophenyl)arylmethanes and bis(4-dimethaminophenyl)alkanes is described. In the presence of an aqueous solution of NaICl2, the reaction of arenes with aromatic aldehydes gives corresponding triarylmethane derivatives regioselectively in moderate to good yields. The method is also useful for the preparation of diarylalkane derivatives by using aliphatic aldehydes. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.
Alkylidene Transfer from Monochloroalkylmercury(II) Compounds to Aromatic Amines; Selective C-Alkylation
Barluenga, Jose,Campos, Pedro J.,Roy, Miguel A.,Asensio, Gregorio
, p. 1420 - 1426 (2007/10/02)
αα-Diarylalkane derivatives have been synthesized from monochloroalkylmercury(II) compounds in a noncarbenoid alkylidene transfer reaction which takes place selectively on the aromatic ring.A mechanism is suggested for this process.Intermediate products are prepared by alternative routes to ascertain their participation in the course of the reaction.As a consequence, two different aryl groups can be successively incorporated into the alkane molecule.
