From J. Am. Chem. Soc
Hi, everyone! Those who often engage in synthesis know that nitrogen, oxygen, and sulfur heterocyclobutanes are very important molecular building blocks, frequently appearing in various drug molecular structures. Previously, I shared an article on the photochemical synthesis of oxazetidines from alcohols in just one step. Can other cyclobutane frameworks be synthesized quickly? Of course, this issue recommends:
“A Unified Synthetic Approach to N, O, S, C Cyclobutanes”
From J. Am. Chem. Soc
⭐Highlights⭐
【1】This method utilizes S-iodomethylthianthrene salt as a carbon-adding reagent, achieving the iodination and thianthrene methyl dual functionalization of alkenes under photochemical conditions, followed by the addition of nucleophiles through nucleophilic substitution, resulting in a one-pot synthesis of N, O, S, C cyclobutanes;
【2】The method has a wide range of alkenes, including various terminal alkenes such as styrene and aliphatic terminal alkenes;
【3】A variety of nucleophiles can be used, including aliphatic primary amines, aromatic primary amines, silver trifluoroacetate, sodium sulfide, and active methylene compounds, all of which can participate in the reaction to yield the corresponding N, O, S, C cyclobutanes;
【4】The synthesis of S-iodomethylthianthrene salt is convenient, as it is a solid reagent that can be synthesized in one step through the following reaction;
【5】The photocatalyst used in the reaction is a commercial reagent, inexpensive and readily available;
【6】A low-cost photocatalytic reactor can use the 20W light reactor from Beijing Nuozhi Technology, and test tubes can be placed in an oil bath or parallel reaction apparatus for temperature control, making it convenient and practical.
⭐References⭐
A Unified Synthetic Approach to 2-Alkyl Azetidines, Oxetanes, Thietanes and Cyclobutanes from Unactivated Alkenes
Louis Buck, Maria Pelosi, Subhasis Paul, Emilie Wheatley, Adam Richardson, Soumen Ghosh, Francesca Sardelli, Mattia Silvi
J. Am. Chem. Soc. 2025, XXXX, XXX, XXX-XXX
DOI : 10.1021/jacs.5c11758