55861-15-9

Basic information

• Product Name: C₂₃H₂₀
• CAS NO: 55861-15-9
• Molecular Weight: 296.412
• Mol File: 55861-15-9.mol

Chemical Properties

• CAS DataBase Reference: C₂₃H₂₀(CAS DataBase Reference)
• NIST Chemistry Reference: C₂₃H₂₀(55861-15-9)
• EPA Substance Registry System: C₂₃H₂₀(55861-15-9)

Safety Data

• Hazardous Substances Data: 55861-15-9(Hazardous Substances Data)

Upstream product

• 100-42-5 styrene 
• 29571-19-5 1,1-diphenylprop-1-en-2-yl trifluoromethanesulfonate 

Relevant articles and documents

Selective arylation and vinylation at the α position of vinylarenes

In intermolecular Heck reactions of styrene and vinylarenes, the aryl and vinyl groups routinely insert at the β position. However, selective insertion at the α position has been very rare. Herein, we provide a missing piece in the palette of Heck reaction, which gave >20:1 α selectivity. The key to our success is a new ferrocene 1,1′-bisphosphane (dnpf) that carries 1-naphthyl groups. Our mechanistic studies revealed that the high α selectivity is partly attributable to the steric effect of dnpf. The rigid and bulky 1-naphthyl groups of dnpf sterically disfavor β insertion. What the Heck! In intermolecular Heck reactions, insertion at the β position of aromatic olefins is very common, but reversal of the selectivity for selective α insertion has been a longstanding problem. A general method to couple aryl and vinyl triflates with aromatic olefins in >20:1 α selectivity is presented. The key to this successful approach is a new ferrocene bisphosphane with naphthyl groups on the phosphorus atom (see scheme; OTf=triflate). Copyright