22020-69-5Relevant articles and documents
Visible light bromide catalysis for oxazoline, pyrrolidine, and dihydrooxazine synthesesviaCsp3-H functionalizations
Kaur, Navdeep,Ziegelmeyer, Elizabeth C.,Farinde, Olutayo N.,Truong, Jonathon T.,Huynh, Michelle M.,Li, Wei
supporting information, p. 10387 - 10390 (2021/10/14)
A catalytic benzylic Csp3-H functionalization protocol is described here. This visible light-mediated process is centered on the utilization of a bromide catalyst and oxidant to generate a nitrogen (N)-centered radical for a site-selective hydrogen atom transfer (HAT) process. This strategy enabled the unconventional syntheses of a number of N-heterocycles dependent on the amide identity. We also discovered a nucleophilicity-dependent kinetic resolution for stereochemical differentiation of Csp3-H bonds that enabled the stereoselective synthesis ofcis- andtrans-oxazolines.
Synthesis of Nitrogen-Containing Heterocycles through Catalytic Dehydrative Cyclization Reactions
Rodriguez Del Rey, Freddy O.,Floreancig, Paul E.
supporting information, p. 150 - 154 (2021/01/09)
Re2O7 in hexafluoroisopropyl alcohol provides access to cationic intermediates from alcohols through the intermediacy of perrhenate esters. This manuscript describes the application of the system to the formation of a number of weakly basic heterocyclic systems through dehydration reactions and intramolecular nucleophilic addition. The influence of the substrate structure on the reaction rates and stereocontrol is discussed with respect to intermediate ion pairs.
Visible-Light-Promoted Metal-Free Aerobic Hydroxyazidation of Alkenes
Yang, Bo,Lu, Zhan
, p. 8362 - 8365 (2017/12/08)
A highly efficient visible-light-promoted metal-free aerobic hydroxyazidation of alkenes has been developed. This protocol was operationally simple with broad substrate scope using relatively simple and readily available starting materials, such as alkene