title: Copper-Catalyzed Alkylation of Nitroalkanes with α-Bromonitriles: Synthesis of β-Cyanonitroalkanes.
abstract: 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 complex cyanoalkenes and 5-aminoisoxazoles.
authors: Department of Chemistry and Biochemistry, University of Delaware , Newark, Delaware 19716, United States.
authors: Kirk W
authors: KW
authors: Shimkin
authors: Department of Chemistry and Biochemistry, University of Delaware , Newark, Delaware 19716, United States.
authors: Peter G
authors: PG
authors: Gildner
authors: Department of Chemistry and Biochemistry, University of Delaware , Newark, Delaware 19716, United States.
authors: Donald A
authors: DA
authors: Watson
mesh_terms: D000473:Alkanes / Q000138:chemical synthesis* / Q000737:chemistry; D000478:Alkylation; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003959:Diamines / Q000138:chemical synthesis* / Q000737:chemistry; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D009574:Nitro Compounds / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000473:Alkanes; D003959:Diamines; D006842:Hydrocarbons, Brominated; D009570:Nitriles; D009574:Nitro Compounds; D003300:Copper