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Copper-Catalyzed Propargylation of Nitroalkanes.

ABSTRACT: 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.

SUBMITTER: Kim RS

PROVIDER: S-EPMC7579671 | biostudies-literature | 2020 Oct

REPOSITORIES: biostudies-literature

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Copper-Catalyzed Propargylation of Nitroalkanes.

Kim Raphael S RS Dinh-Nguyen Linh V LV Shimkin Kirk W KW Watson Donald A DA

Organic letters 20201002 20

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 <i>N</i> ...[more]

PMID: 33006901

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