131523-32-5Relevant articles and documents
Cuprous Oxide Catalyzed Oxidative C-C Bond Cleavage for C-N Bond Formation: Synthesis of Cyclic Imides from Ketones and Amines
Wang, Min,Lu, Jianmin,Ma, Jiping,Zhang, Zhe,Wang, Feng
, p. 14061 - 14065 (2015)
Selective oxidative cleavage of a C-C bond offers a straightforward method to functionalize organic skeletons. Reported herein is the oxidative C-C bond cleavage of ketone for C-N bond formation over a cuprous oxide catalyst with molecular oxygen as the oxidant. A wide range of ketones and amines are converted into cyclic imides with moderate to excellent yields. In-depth studies show that both α-C-H and β-C-H bonds adjacent to the carbonyl groups are indispensable for the C-C bond cleavage. DFT calculations indicate the reaction is initiated with the oxidation of the α-C-H bond. Amines lower the activation energy of the C-C bond cleavage, and thus promote the reaction. New insight into the C-C bond cleavage mechanism is presented.
The first preparation of α-functionalized benzylamine
Cho, Su-Dong,Kim, Hyeung-Jae,Ahn, Chuljin,Falckb,Shin, Dong-Soo
, p. 8215 - 8217 (1999)
We have investigated the α-acetoxylation of benzylamine derivatives 4 from substituted benzylphthalimide 3 using NBS/AcONa/AcOH in chlorobenzene at reflux.
Alkoxide-Catalyzed Hydrosilylation of Cyclic Imides to Isoquinolines via Tandem Reduction and Rearrangement
Wu, Xiaoyu,Ding, Guangni,Yang, Liqun,Lu, Wenkui,Li, Wanfang,Zhang, Zhaoguo,Xie, Xiaomin
supporting information, p. 5610 - 5613 (2018/09/12)
An alkoxide-catalyzed hydrosilylation of cyclic imides to isoquinolines was realized via tandem reduction and rearrangement. Using TMSOK as the catalyst and (EtO)2MeSiH as the reductant, a series of cyclic imides containing different functional groups were reduced to the corresponding 3-aryl isoquinolines in moderate to good yields. The scenario of the reaction pathway was supposed to involve the reduction of imides to ω-hydroxylactams, which underwent rearrangement in the presence of a base catalyst, and then the carbonyl reduction, followed by siloxy elimination.
An efficient synthesis of N-substituted phthalimides using SiO2-tpy-Nb as heterogeneous and reusable catalyst
Wan, Li,Sun, Xiaoning,Shi, Songjie,Zhang, Jiawei,Li, Xin,Li, Zhenjiang,Guo, Kai
, p. 30 - 34 (2016/09/28)
A novel and efficient heterogeneous catalyst SiO2-tpy-Nb was developed, and its application in the preparation of N-substituted phthalimides from o-phthalic acids or anhydrides with amines provides the desired products in good to excellent yields. The catalyst was stable and recoverable for eight consecutive cycles without a significant loss in its activity. Furthermore, the catalyst is applicable in continuous flow which indicates its potential utilization in industrialization.
