626-62-0Relevant articles and documents
Visible-light-mediated multicomponent reaction for secondary amine synthesis
Wang, Xiaochen,Zhu, Binbing,Dong, Jianyang,Tian, Hao,Liu, Yuxiu,Song, Hongjian,Wang, Qingmin
supporting information, p. 5028 - 5031 (2021/05/28)
The widespread presence of secondary amines in agrochemicals, pharmaceuticals, natural products, and small-molecule biological probes has inspired efforts to streamline the synthesis of molecules with this functional group. Herein, we report an operationally simple, mild protocol for the synthesis of secondary amines by three-component alkylation reactions of imines (generated in situ by condensation of benzaldehydes and anilines) with unactivated alkyl iodides catalyzed by inexpensive and readily available Mn2(CO)10. This protocol, which is compatible with a wide array of sensitive functional groups and does not require a large excess of the alkylating reagent, is a versatile, flexible tool for the synthesis of secondary amines.
A Metal-Free, Photocatalytic Method for Aerobic Alkane Iodination
Anna, Jessica M.,Goldberg, Karen I.,Hirscher, Nathanael A.,Ohri, Nidhi,Schelter, Eric J.,Yang, Qiaomu,Zhou, Jiawang
supporting information, p. 19262 - 19267 (2021/11/30)
Halogenation is an important alkane functionalization strategy, but O2 is widely considered the most desirable terminal oxidant. Here, the aerobic iodination of alkanes, including methane, was performed using catalytic [nBu4N]Cl and light irradiation (390 nm). Up to 10 turnovers of CH3I were obtained from CH4 and air, using a stop-flow microtubing system. Mechanistic studies using cyclohexane as the substrate revealed important details about the iodination reaction. Iodine (I2) serves multiple roles in the catalysis: (1) as the alkyl radical trap, (2) as a precursor for the light absorber, and (3) as a mediator of aerobic oxidation. The alkane activation is attributed to Cl? derived from photofragmentation of the electron donor-acceptor complex of I2 and Cl-. The kinetic profile of cyclohexane iodination showed that aerobic oxidation of I3- to produce I2 in CH3CN is turnover-limiting.
Rhodium-Catalyzed Generation of Anhydrous Hydrogen Iodide: An Effective Method for the Preparation of Iodoalkanes
Zeng, Chaoyuan,Shen, Guoli,Yang, Fan,Chen, Jingchao,Zhang, Xuexin,Gu, Cuiping,Zhou, Yongyun,Fan, Baomin
supporting information, p. 6859 - 6862 (2018/10/25)
The preparation of anhydrous hydrogen iodide directly from molecular hydrogen and iodine using a rhodium catalyst is reported for the first time. The anhydrous hydrogen iodide generated was proven to be highly active in the transformations of alkenes, phenyl aldehydes, alcohols, and cyclic ethers to the corresponding iodoalkanes. Therefore, the present methodology not only has provided convenient access to anhydrous hydrogen iodide but also offers a practical preparation method for various iodoalkanes in excellent atom economy.