Kim Raphael S, Dinh-Nguyen Linh V, Shimkin Kirk W, Watson Donald A
Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, United States.
Org Lett. 2020 Oct 16;22(20):8106-8110. doi: 10.1021/acs.orglett.0c03061. Epub 2020 Oct 2.
Using a commercially available, inexpensive, and abundant copper catalyst system, an efficient α-functionalization of nitroalkanes with propargyl bromides is now established. This mild and robust method is highly functional group tolerant and provides straightforward access to complex secondary and tertiary homopropargylic nitroalkanes. Moreover, the utility of these α-propargylated nitroalkanes is demonstrated through downstream functionalization to biologically relevant, five-membered -heterocycles such as pyrroles and 2-pyrrolines.
利用一种市售的、廉价且丰富的铜催化剂体系,现已实现了硝基烷烃与炔丙基溴的高效α-官能化反应。这种温和且稳健的方法对官能团具有高度耐受性,能直接合成复杂的仲和叔高炔丙基硝基烷烃。此外,通过将这些α-炔丙基化硝基烷烃进行下游官能化反应,制得与生物相关的五元杂环化合物,如吡咯和2-吡咯啉,从而证明了其用途。