Related Experiment Video
Updated: Aug 25, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Sequential ring-closing metathesis and silicon-assisted cross-coupling reactions: stereocontrolled synthesis of
1Roger Adams Laboratory, Department of Chemistry, University of Illinois, 600 South Mathews Avenue, Urbana, IL 61801, USA. denmark@scs.uiuc.edu
Abstract:
A sequential ring-closing metathesis/silicon-assisted cross-coupling sequence has been developed. Alkenyldimethylsilyl ethers of omega-unsaturated alcohols undergo facile ring closure with Schrock's catalyst to afford five-, six-, and seven-membered cycloalkenylsiloxanes bearing substituents on both alkenyl carbons. These siloxanes were highly effective coupling partners with various aryl and alkenyl halides and in the presence of Pd(0) afforded styrenes and dienes in high yield and specificity and with good functional group compatibility.
More Related Videos
06:31Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
Published on: November 27, 2015
07:50Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Related Concept Videos
Preparation of Alcohols via Substitution Reactions
Alcohols can be synthesized from alkyl halides via nucleophilic substitution reactions. The highly polar carbon-halogen bond in the substrate makes halide a good leaving group. The hydroxide ion or water can act as a nucleophile to take the place of halide and form an alcohol. The substitution reactions occur via two different reaction pathways, SN1 or SN2, depending on the nature of carbon attached to the halide.
Primary alcohols are synthesized from primary alkyl halides, and the...
Acid-Catalyzed Ring-Opening of Epoxides
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement