3540-95-2Relevant articles and documents
Migratory Arylboration of Unactivated Alkenes Enabled by Nickel Catalysis
Wang, Wang,Ding, Chao,Li, Yangyang,Li, Zheqi,Li, Yuqiang,Peng, Long,Yin, Guoyin
supporting information, p. 4612 - 4616 (2019/03/13)
An unprecedented arylboration of unactivated terminal alkenes, featuring 1,n-regioselectivity, has been achieved by nickel catalysis. The nitrogen-based ligand plays an essential role in the success of this three-component reaction. This transformation displays good regioselectivity and excellent functional-group tolerance. In addition, the incorporation of a boron group into the products provides substantial opportunities for further transformations. Also demonstrated is that the products can be readily transformed into pharmaceutically relevant molecules. Unexpectedly, preliminary mechanistic studies indicate that although the metal migration favors the α-position of boron, selective and decisive bond formation is favored at the benzylic position.
Tandem superelectrophilic hydroarylation of CC bond and carbonyl reduction in cinnamides: Synthetic rout to 3,3-diarylpropylamines, valuable pharmaceuticals
Zakusilo, Dmitry N.,Ryabukhin, Dmitry S.,Boyarskaya, Irina A.,Yuzikhin, Oleg S.,Vasilyev, Aleksander V.
, p. 102 - 108 (2015/02/02)
Cinnamides ArCHCHCONRR′ in reactions with arenes Ar′H under the action of Bronsted (TfOH, FSO3H) or Lewis (AlBr3) superacids at rt for 1-2 h give CC bond hydroarylation products ArAr′CHCH2CONRR′ in yields of 63-98%. Reduction (LiAlH4/Et2O) of carbonyl group in the latter results in the formation of 3,3-diarylpropylamines ArAr′CHCH2CH2NRR′, valuable drugs. The reaction intermediates, superelectrophilic dications ArC+H-CH2C(OH+)NRR′, have been characterized by DFT calculations in terms of global electrophilicity index, natural charges, and atomic orbitals contributions.
Cascade synthesis of fenpiprane and related pharmaceuticals via rhodium-catalyzed hydroaminomethylation
Li, Shengkun,Huang, Kexuan,Zhang, Jiwen,Wu, Wenjun,Zhang, Xumu
supporting information, p. 1036 - 1039 (2013/04/23)
A novel rhodium catalytic system with Naphos as ligand was developed for an efficient hydroaminomethylation of 1,1-diphenylethene under relatively mild conditions. This will allow for an atom-economic and environmentally benign synthesis of fenpiprane and related pharmaceuticals.
