Open AccessCopper-Catalyzed Propargylation of Nitroalkanes
Author(s) -
Raphael Kim,
Linh V Dinh-Nguyen,
Kirk W. Shimkin,
Donald A. Watson
Publication year - 2020
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.0c03061
Subject(s) - propargyl , chemistry , surface modification , catalysis , combinatorial chemistry , copper , functional group , reaction conditions , organic chemistry , polymer
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.