title: Cyclic Alkenenitriles: Copper-Catalyzed Deconjugative α-Alkylation.
abstract: An amido cuprate formed from CuCN and LDA allows a general deconjugative α-alkylation of cyclic alkenenitriles. Deprotonating cyclic alkenenitriles with LDA-CuCN avoids polymerization that otherwise plagues these alkylations and generates a reactive metalated nitrile for alkylations with a range of carbon and heteroatom electrophiles. The strategy provides an effective synthesis of quaternary 5-, 6-, and 7-membered cycloalk-1-enecarbonitriles substituted on the nitrile-bearing carbon.
authors.affiliation: Department of Chemistry, Duquesne University , Pittsburgh, Pennsylvania 15282, United States.
authors.forename: Xun
authors.initials: X
authors.lastname: Yang
authors.affiliation: Department of Chemistry, University of Oklahoma , Norman, Oklahoma 73019, United States.
authors.forename: Dinesh
authors.initials: D
authors.lastname: Nath
authors.affiliation: Department of Chemistry, The University of North Carolina at Charlotte , Charlotte, North Carolina 28223, United States.
authors.forename: Jared
authors.initials: J
authors.lastname: Morse
authors.affiliation: Department of Chemistry, The University of North Carolina at Charlotte , Charlotte, North Carolina 28223, United States.
authors.forename: Craig
authors.initials: C
authors.lastname: Ogle
authors.affiliation: Department of Chemistry, Ataturk University , 25240 Erzurum, Turkey.
authors.forename: Emine
authors.initials: E
authors.lastname: Yurtoglu
authors.affiliation: Department of Chemistry, Ataturk University , 25240 Erzurum, Turkey.
authors.forename: Ramazan
authors.initials: R
authors.lastname: Altundas
authors.affiliation: Department of Chemistry, Drexel University , Philadelphia, Pennsylvania 19104, United States.
authors.forename: Fraser
authors.initials: F
authors.lastname: Fleming