136408-23-6Relevant academic research and scientific papers
Selective Mono- and Polymethylene Homologations of Copper Reagents Using (Iodomethyl)zinc Iodide
Sidduri, AchyuthaRao,Rozema, Michael J.,Knochel, Paul
, p. 2694 - 2713 (2007/10/02)
A wide range of unsaturated aryl-, alkenyl-, alkynylcopper compounds can be selectively homologated by a methylene unit using (iodomethyl)zinc iodide or bis(iodomethyl)zinc.These reactions allow the generation of mixed allylic zinc-copper compounds which can be efficiently trapped with carbonyl compounds.An application to a general preparation of functionalized α-methylene-γ-butyrolactones is described.The homologation of alkynylcoppers with (iodomethyl)zinc iodide allows a one-pot preparation of propargylic copper reagents which in the presence of a carbonyl compound provide various homopropargylic alcohols in excellent yields.In the absence of an electrophile, a clean quadruple methylene homologation of alkynylcoppers occurs to furnish dienic copper reagents.The homologation of other types of copper reagents is also possible, and carbanions at the α-position to amines as well as homoenolates of aldehydes or ketones can also be prepared by this method.
Preparation and Reaction of Zinc and Copper Organometallics Bearing Acidic Hydrogens
Knoess, H. Peter,Furlong, Michael T.,Rozema, Michael J.,Knochel, Paul
, p. 5974 - 5978 (2007/10/02)
Organozinc and copper ragents bearing unprotected primary or secondary amines or amides or a terminal acetylenic proton were prepared and reacted with various electrophiles in good yields.
