2211-66-7Relevant articles and documents
Electrochemical dehydrogenation of 1,2,3,4-tetrahydroisoquinoline to 3,4-dihydroisoquinoline
Okimoto, Mitsuhiro,Takahashi, Yukio,Numata, Kaori,Sasaki, Gaku
, p. 371 - 375 (2005)
Dehydrogenation of 1,2,3,4-tetrahydroisoquinoline to 3,4-dihydroisoquinoline was carried out using an electrochemical method in the presence of KI. In this method, the iodide ion presumably played an important role as an electron carrier.
Transient imine as a directing group for the metal-free o-C-H borylation of benzaldehydes
Rej, Supriya,Chatani, Naoto
supporting information, p. 2920 - 2929 (2021/03/01)
Organoboron reagents are important synthetic intermediates and have wide applications in synthetic organic chemistry. The selective borylation strategies that are currently in use largely rely on the use of transition-metal catalysts. Hence, identifying much milder conditions for transition-metal-free borylation would be highly desirable. We herein present a unified strategy for the selective C-H borylation of electron-deficient benzaldehyde derivatives using a simple metal-free approach, utilizing an imine transient directing group. The strategy covers a wide spectrum of reactions and (i) even highly sterically hindered C-H bonds can be borylated smoothly, (ii) despite the presence of other potential directing groups, the reaction selectively occurs at the o-C-H bond of the benzaldehyde moiety, and (iii) natural products appended to benzaldehyde derivatives can also give the appropriate borylated products. Moreover, the efficacy of the protocol was confirmed by the fact that the reaction proceeds even in the presence of a series of external impurities.
Rhodium catalyzed multicomponent dehydrogenative annulation: one-step construction of isoindole derivatives
Cheng, Biao,Lyu, Hairong,Quan, Yangjian,Xie, Zuowei
supporting information, p. 7930 - 7933 (2021/08/17)
A strategy for one-pot synthesis of isoindoles is describedviaa catalytic multicomponent dehydrogenative annulation of diarylimines, vinyl ketones and simple amines. In the presence of a rhodium catalyst and Cu oxidant, four C-H and two N-H bonds are activated along with the formation of one new C-C and two new C-N bonds, leading to a series of isoindole derivatives in good to very high isolated yields.
Redox-Neutral Imination of Alcohol with Azide: A Sustainable Alternative to the Staudinger/Aza-Wittig Reaction
Li, Huaifeng,Lupp, Daniel,Das, Pradip K.,Yang, Li,Gon?alves, Théo P.,Huang, Mei-Hui,El Hajoui, Marwa,Liang, Lan-Chang,Huang, Kuo-Wei
, p. 4071 - 4076 (2021/04/12)
The traditional Staudinger/aza-Wittig reaction represents one of the most powerful tools for imine formation. However, for this multistep procedure, the sacrificial phosphine has to be used, resulting in difficulties in the purification process and waste disposal at the same time. Here, we report a redox-neutral azide-alcohol imination methodology enabled by a base-metal nickel PN3 pincer catalyst. The one-step, waste-free, and high atom-economical features highlight its advantages further. Moreover, mechanistic insight suggests a non-metal-ligand cooperation pathway based on the observation of an intermediate and density functional theory calculations.