Stereospecific cross-coupling of alpha-(thiocarbamoyl)organostannanes with alkenyl, aryl, and heteroaryl iodides.
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.
Falck
J R
JR
Departments of Biochemistry and Pharmacology, University of Texas Southwestern Medical Center, Dallas, Texas 75390, USA. j.falck@utsouthwestern.edu
Patel
Paresh K
PK
Bandyopadhyay
Anish
A
D000475:Alkenes / Q000737:chemistry*; D006847:Hydrocarbons, Iodinated / Q000737:chemistry*; D009947:Organotin Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000475:Alkenes; D006847:Hydrocarbons, Iodinated; D009947:Organotin Compounds