856210-99-6Relevant academic research and scientific papers
De Novo Synthesis of Phenols and Naphthols through Oxidative Cycloaromatization of Dienynes
Rong, Ming-Guang,Qin, Tian-Zhu,Liu, Xin-Rui,Wang, Hong-Fa,Zi, Weiwei
supporting information, p. 6289 - 6293 (2018/10/09)
In this work, a rhodium-catalyzed oxidative cycloaromatization of dienynes, which provides a highly straightforward and efficient way to access polysubstituted naphthols and phenols under mild conditions, is described. Challenged electron-withdrawing groups are well tolerated in this protocol, and late-stage phenyl ring formation is demonstrated.
Iodoarene-Catalyzed Stereospecific Intramolecular sp3 C-H Amination: Reaction Development and Mechanistic Insights
Zhu, Chendan,Liang, Yong,Hong, Xin,Sun, Heqing,Sun, Wei-Yin,Houk,Shi, Zhuangzhi
supporting information, p. 7564 - 7567 (2015/06/30)
A new strategy is reported for intramolecular sp3 C-H amination under mild reaction conditions using iodoarene as catalyst and m-CPBA as oxidant. This C-H functionalization involving iodine(III) reagents generated in situ occurs readily at sterically hindered tertiary C-H bonds. DFT (M06-2X) calculations show that the preferred pathway involves an iodonium cation intermediate and proceeds via an energetically concerted transition state, through hydride transfer followed by the spontaneous C-N bond formation. This leads to the experimentally observed amination at a chiral center without loss of stereochemical information.
