66310-10-9Relevant articles and documents
Visible-Light-Induced Regioselective Deaminative Alkylation of Coumarins via Photoredox Catalysis
Tao, Maoling,Wang, An-Jun,Guo, Peng,Li, Weipiao,Zhao, Liang,Tong, Jie,Wang, Haoyang,Yu, Yanbo,He, Chun-Yang
supporting information, p. 24 - 29 (2021/10/19)
3-Alkylated coumarins have many applications in medicinal chemistry, however, methods access to such structures are still limited. Herein, we report a site-selective photocatalytic deaminative alkylation of coumarins utilizing pyridinium-activated aliphatic primary amines as alkylation reagents. The protocol was highlighted by its mild reaction conditions, operational simplicity, and broad functional group compatibility. Moreover, this strategy enables late-stage modification of some pharmaceuticals and natural products, thus providing an appealing approach to valuable molecules in medicinal chemistry. (Figure presented.).
Sulfinates from Amines: A Radical Approach to Alkyl Sulfonyl Derivatives via Donor-Acceptor Activation of Pyridinium Salts
Andrews, Jonathan A.,Pantaine, Lo?c R. E.,Palmer, Christopher F.,Poole, Darren L.,Willis, Michael C.
supporting information, p. 8488 - 8493 (2021/11/01)
Synthetically versatile alkyl sulfinates can be prepared from readily available amines, using Katritzky pyridinium salt intermediates. In a catalyst-free procedure, primary, secondary, and benzylic alkyl radicals are generated by photoinduced or thermally induced single-electron transfer (SET) from an electron donor-acceptor (EDA) complex, and trapped by SO2 to generate sulfonyl radicals. Hydrogen atom transfer (HAT) from Hantzsch ester gives alkyl sulfinate products, which are used to prepare a selection of medicinal chemistry relevant sulfonyl-containing motifs.
Biocompatible Photoinduced Alkylation of Dehydroalanine for the Synthesis of Unnatural α-Amino Acids
Delgado, José A. C.,Correia, José T. M.,Pissinati, Emanuele F.,Paix?o, Márcio W.
supporting information, p. 5251 - 5255 (2021/07/20)
A site-selective alkylation of dehydroalanine to access protected unnatural amino acids is described. The protocol is characterized by the wide nature of alkyl radicals employed, mild conditions, and functional group compatibility. This protocol is further extended to access peptides, late-stage functionalization of pharmaceuticals, and enantioenriched amino acids.