Direct Synthesis of α-Iodoenones by IPy 2 BF 4-Promoted Rearrangement of Propargylic Esters

Tatiana Suárez-Rodríguez, Ángel L Suárez-Sobrino, Alfredo Ballesteros

J Org Chem. 2018 Oct 19;83(20):12575-12583.

PMID: 30247033

Abstract:

A direct access to α-iodoeones from iodonium ion and propargylic tosylates or acetates is described. Bis(pyridine) iodonium tetrafluoroborate (IPy2BF4, Barluenga's reagent) promotes the rearrangement of these propargylic alcohol derivatives in mild conditions. The transformation gives β-unsubstituted, β-monosubstituted, and β,β-disubstituted α-iodoenones in high yields. β-Substituted α-iodoenones are obtained with excellent ( Z)-selectivity.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP33462816	Cyclopropyldiphenylsulfonium tetrafluoroborate		33462-81-6	Price