title: Stereospecific cross-coupling of alpha-(thiocarbamoyl)organostannanes with alkenyl, aryl, and heteroaryl iodides.
abstract: Racemic and scalemic PTC-protected alpha-hydroxystannanes cross-couple with alkenyl/aryl/heteroaryl iodides in moderate to good yields using copper(I) thiophene-2-carboxylate (CuTC) in THF at or below room temperature. Simple aryl iodides and 1-iodocyclohexene, two classes of electrophiles that typically react sluggishly, are also good substrates. Cross-couplings proceed with retention of configuration at the alkenyl- and stannyl-substituted stereocenters.
authors.affiliation: Departments of Biochemistry and Pharmacology, University of Texas Southwestern Medical Center, Dallas, Texas 75390, USA. j.falck@utsouthwestern.edu
authors.forename: J R
authors.initials: JR
authors.lastname: Falck
authors.forename: Paresh K
authors.initials: PK
authors.lastname: Patel
authors.forename: Anish
authors.initials: A
authors.lastname: Bandyopadhyay
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D006847:Hydrocarbons, Iodinated / Q000737:chemistry*; D009947:Organotin Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D006847:Hydrocarbons, Iodinated; D009947:Organotin Compounds