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DOI: 10.1055/s-0034-1379250
Design of Molecular Transformations Based on the Concerted Function of Two Zinc Atoms in Bis(iodozincio)methane
Publikationsverlauf
Received: 18. Juli 2014
Accepted after revision: 15. September 2014
Publikationsdatum:
12. November 2014 (online)


Abstract
Bis(iodozincio)methane, prepared from diiodomethane and zinc metal in the presence of a lead catalyst, is capable of performing several unique molecular transformations. It can operate not only as a dianion, but also as a bidentate Lewis acid. In this account, the methylenation of carbonyl compounds, nucleophilic cyclopropanation reactions, 1,4-addition reactions of bis(iodozincio)methane, and reduction reactions of π-allylpalladium are discussed, along with the associated density functional theory calculations.
1 Introduction
2 Methylenation of Carbonyl Compounds
3 Nucleophilic Cyclopropanation
3.1 Cyclopropanation of 1,2-Diketones
3.2 Asymmetric Construction of Quaternary Carbon Atoms by Stereospecific Cyclopropanation
4 1,4-Addition Reactions of Bis(iodozincio)methane
4.1 Three-Atom Ring-Contraction Reaction
4.2 Enolate–Homoenolate Intermediates and Their Reactions
5 Reduction of π-Allylpalladium Derivatives
6 Conclusions and Outlook