6709-42-8Relevant articles and documents
Silver-Catalyzed N-H Functionalization of Aryl/Aryl Diazoalkanes with Anilines
He, Feifei,Empel, Claire,Koenigs, Rene M.
supporting information, p. 6719 - 6723 (2021/09/13)
Herein, we report on the N-H functionalization reaction of primary and secondary anilines with diaryldiazoalkanes using simple AgPF6 as catalyst. We demonstrated broad applicability in the reaction of diaryldiazoalkanes with different anilines (31 examples, up to 97% yield). Furthermore, we propose a possible reaction mechanism for the N-H functionalization.
Borane-Catalyzed Chemoselectivity-Controllable N-Alkylation and ortho C-Alkylation of Unprotected Arylamines Using Benzylic Alcohols
Meng, Shan-Shui,Tang, Xiaowen,Luo, Xiang,Wu, Ruibo,Zhao, Jun-Ling,Chan, Albert S. C.
, p. 8397 - 8403 (2019/09/03)
An unprecedented protocol for the efficient and highly chemoselective alkylation of unprotected arylamines using alcohols catalyzed by B(C6F5)3 has been developed. The reaction gives N-alkylated products and ortho C-alkylated products in different solvents in good chemoselectivities and yields. Control experiments and DFT calculations indicated that the borane underwent alcohol/arylamine exchange to ensure catalytic activity, and a possible mechanism involving a carbocation is proposed.
Hydrogen-Borrowing Amination of Secondary Alcohols Promoted by a (Cyclopentadienone)iron Complex
Aiolfi, Francesco,Bai, Xishan,Cettolin, Mattia,Dal Corso, Alberto,Gennari, Cesare,Piarulli, Umberto,Pignataro, Luca
, p. 3545 - 3555 (2019/09/09)
Thanks to a highly active catalyst, the scope of the (cyclopentadienone)iron complex-promoted 'hydrogen-borrowing' (HB) amination has been expanded to secondary alcohols, which had previously been reported to react only in the presence of large amounts of co-catalysts. A range of cyclic and acyclic secondary alcohols were reacted with aromatic and aliphatic amines giving fair to excellent yields of the substitution products. The catalyst was also able to promote the cyclization of diols bearing a secondary alcohol group with primary amines to generate saturated N-heterocycles.