title: Stereospecific Suzuki, Sonogashira, and Negishi coupling reactions of N-alkoxyimidoyl iodides and bromides.
abstract: A high-yielding stereospecific route to the synthesis of single geometric isomers of diaryl oxime ethers through Suzuki coupling of N-alkoxyimidoyl iodides is described. This reaction occurs with complete retention of the imidoyl halide geometry to give single E- or Z-isomers of diaryl oxime ethers. The Sonogashira coupling of N-alkoxyimidoyl iodides and bromides with a wide variety of terminal alkynes to afford single geometric isomers of aryl alkynyl oxime ethers has also been developed. Several of these reactions proceed through copper-free conditions. The Negishi coupling of N-alkoxyimidoyl halides is introduced. The E and Z configurations of nine Suzuki-coupling products and two Sonogashira-coupling products were confirmed by X-ray crystallography.
authors.affiliation: Department of Chemistry and Physics, Southeastern Louisiana University, SLU 10878, Hammond, Louisiana 70402, USA. ddolliver@selu.edu
authors.forename: Debra D
authors.initials: DD
authors.lastname: Dolliver
authors.forename: Bijay T
authors.initials: BT
authors.lastname: Bhattarai
authors.forename: Arjun
authors.initials: A
authors.lastname: Pandey
authors.forename: Megan L
authors.initials: ML
authors.lastname: Lanier
authors.forename: Amber S
authors.initials: AS
authors.lastname: Bordelon
authors.forename: Sarju
authors.initials: S
authors.lastname: Adhikari
authors.forename: Jordan A
authors.initials: JA
authors.lastname: Dinser
authors.forename: Patrick F
authors.initials: PF
authors.lastname: Flowers
authors.forename: Veronica S
authors.initials: VS
authors.lastname: Wills
authors.forename: Caroline L
authors.initials: CL
authors.lastname: Schneider
authors.forename: Kevin H
authors.initials: KH
authors.lastname: Shaughnessy
authors.forename: Jane N
authors.initials: JN
authors.lastname: Moore
authors.forename: Steven M
authors.initials: SM
authors.lastname: Raders
authors.forename: Timothy S
authors.initials: TS
authors.lastname: Snowden
authors.forename: Artie S
authors.initials: AS
authors.lastname: McKim
authors.forename: Frank R
authors.initials: FR
authors.lastname: Fronczek