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Copper-Catalyzed Alkylation of Nitroalkanes with ?-Bromonitriles: Synthesis of ?-Cyanonitroalkanes.

ABSTRACT: Copper catalysis now enables the efficient C-alkylation of nitroalkanes with ?-bromonitriles. Using a simple and inexpensive catalyst, this process provides access to ?-cyanonitroalkanes. The method is highly tolerant of various functional groups and substitution patterns. These functionally dense products serve as orthogonally masked 1,3-diamines, which can be revealed selectively for access to differentially substituted diamines. These products can also be exploited for the formation of complex cyanoalkenes and 5-aminoisoxazoles.

SUBMITTER: Shimkin KW

PROVIDER: S-EPMC4927086 | biostudies-literature | 2016 Mar

REPOSITORIES: biostudies-literature

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Copper-Catalyzed Alkylation of Nitroalkanes with α-Bromonitriles: Synthesis of β-Cyanonitroalkanes.

Shimkin Kirk W KW Gildner Peter G PG Watson Donald A DA

Organic letters 20160211 5

Copper catalysis now enables the efficient C-alkylation of nitroalkanes with α-bromonitriles. Using a simple and inexpensive catalyst, this process provides access to β-cyanonitroalkanes. The method is highly tolerant of various functional groups and substitution patterns. These functionally dense products serve as orthogonally masked 1,3-diamines, which can be revealed selectively for access to differentially substituted diamines. These products can also be exploited for the formation of comple ...[more]

PMID: 26866576

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