Copper-Catalyzed Propargylation of Nitroalkanes.

Autor: Kim RS; Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, United States., Dinh-Nguyen LV; Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, United States., Shimkin KW; Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, United States., Watson DA; Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, United States.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2020 Oct 16; Vol. 22 (20), pp. 8106-8110. Date of Electronic Publication: 2020 Oct 02.
DOI: 10.1021/acs.orglett.0c03061
Abstrakt: 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 N -heterocycles such as pyrroles and 2-pyrrolines.
Databáze: MEDLINE