134627-97-7Relevant 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.
Benzotriazole: A novel synthetic auxiliary
Katritzky, Alan R.,Rachwal, Stanislaw,Hitchings, Gregory J.
, p. 2683 - 2732 (2007/10/02)
Benzotriazole and aldehydes react reversibly to give addition products: in the presence of amines and other NH-compounds water can be eliminated to form products of type Bt-CHR-NR′R″. The latter are versatile intermediates for the preparation of primary, secondary, and tertiary amines and in the alkylation of hydroxylamines, hydrazines, amides, thioamides, and sulfonamides. Polyfunctional amines and other polyfunctional compounds can also be prepared, and they enable significant extending of Mannich reaction. Similar oxygen compounds Bt-CRR′-OR″ enable new syntheses of ethers and esters. Reactions in which benzotriazole is eliminated rather than substituted open up new pathways to enamines, enol ethers, and nitrones. The methodology is capable of extension to a variety of vinylogous systems including benzenoid and heteroaromatic derivatives. In addition to acting as a versatile leaving group, benzotriazolyl residues activate neighboring CH bonds to proton loss and a variety of such applications is described.
Benzotriazole as a Synthetic Auxiliary: Advantageous Syntheses of Substituted Diarylmethanes and Heterocyclic Analogues
Katritzky, Alan R.,Lan, Xiangfu,Lam, Jamshed N.
, p. 4397 - 4403 (2007/10/02)
4-(Benzotriazol-1-ylmethyl)-N,N-dimethylaniline (1b) can be substituted at the CH2 link via lithiation.Both the parent and substituted derivatives react with a variety of electron-rich benzenoid and heteroaromatic compounds in a novel approach to leuco dy
