1135867-81-0Relevant articles and documents
Visible-Light-Enabled Direct Decarboxylative N-Alkylation
Arman, Hadi D.,Dang, Hang T.,Haug, Graham C.,Larionov, Oleg V.,Nguyen, Viet D.,Nguyen, Vu T.,Vuong, Ngan T. H.
supporting information, p. 7921 - 7927 (2020/04/10)
The development of efficient and selective C?N bond-forming reactions from abundant feedstock chemicals remains a central theme in organic chemistry owing to the key roles of amines in synthesis, drug discovery, and materials science. Herein, we present a dual catalytic system for the N-alkylation of diverse aromatic carbocyclic and heterocyclic amines directly with carboxylic acids, by-passing their preactivation as redox-active esters. The reaction, which is enabled by visible-light-driven, acridine-catalyzed decarboxylation, provides access to N-alkylated secondary and tertiary anilines and N-heterocycles. Additional examples, including double alkylation, the installation of metabolically robust deuterated methyl groups, and tandem ring formation, further demonstrate the potential of the direct decarboxylative alkylation (DDA) reaction.
Aerobic intramolecular aminothiocyanation of unactivated alkenes promoted by in situ generated iodine thiocyanate
Feng, Yangyang,Hussain, Muhammad Ijaz,Zhang, Xiaohui,Shi, Jian,Hu, Wen,Xiong, Yan
supporting information, p. 2669 - 2676 (2018/05/04)
Aerobic intramolecular aminothiocyanation of unactivated alkenes has been developed by in situ generated iodine thiocyanate under open-flask conditions. This protocol provides a concise and efficient method for synthesizing SCN-containing pyrrolidine, piperidine and indoline derivatives with isolated yields of up to 87%. Furthermore, mixing iodine and sodium thiocyanate with oxygen afforded iodine thiocyanate (ISCN) and dithiocyanatoiodate [I(SCN)2]- which were testified by liquid chromatography mass spectrometry. A mechanistic investigation indicates that iodonium ion and sulfonium ion intermediates might be involved in this transformation.
An Aminopyridinato Titanium Catalyst for the Intramolecular Hydroaminoalkylation of Secondary Aminoalkenes
D?rfler, Jaika,Bytyqi, Besnik,Hüller, Sascha,Mann, Nicola M.,Brahms, Christian,Schmidtmann, Marc,Doye, Sven
supporting information, p. 2265 - 2276 (2015/07/27)
The easily accessible 2-(methylamino)pyridinato titanium complex initially synthesized by Kempe is used as catalyst for efficient intramolecular hydroaminoalkylation reactions of secondary aminoalkenes. The corresponding reactions of N-aryl-substituted 1-aminohept-6-enes and 1-aminohex-5-enes directly give access to 2-methylcyclohexyl- or 2-methylcyclopentylamines in good yields. In addition, intramolecular hydroaminoalkylations of an N-alkyl-substituted secondary aminoalkene and a geminally β-disubstituted substrate are described for the first time. While all products are formed as mixtures of two diastereoisomers, better trans/cis ratios are observed during the formation of 2-methylcylopentylamines.