Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University , Suzhou 215123, People's Republic of China.
J Org Chem. 2017 Jan 20;82(2):1145-1154. doi: 10.1021/acs.joc.6b02767. Epub 2017 Jan 9.
An efficient method for the modular synthesis of various pyrimidine derivatives by means of the reactions of ketones, aldehydes, or esters with amidines in the presence of an in situ prepared recyclable iron(II)-complex was developed. This operationally simple reaction proceeded with broad functional group tolerance in a regioselective manner via a remarkable unactivated β-C-H bond functionalization. Control experiments were performed to gain deep understanding of the mechanism, and the reactions are likely to proceed through a designed TEMPO complexation/enamine addition/transient α-occupation/β-TEMPO elimination/cyclization sequence.
开发了一种通过酮、醛或酯与脒在原位制备的可回收铁(II)配合物存在下的反应，高效模块化合成各种嘧啶衍生物的方法。该操作简单的反应具有广泛的官能团耐受性，通过显著的未活化的β-C-H 键功能化以区域选择性方式进行。进行了控制实验以深入了解反应机理，该反应可能通过设计的 TEMPO 络合/烯胺加成/瞬态α-占据/β-TEMPO 消除/环化顺序进行。
