Catalytic functionalization of unactivated primary C-H bonds directed by an alcohol was written by Simmons, Eric M.;Hartwig, John F.. And the article was included in Nature (London, United Kingdom) in 2012.Application In Synthesis of N,N-Diethyl-4-iodobenzamide This article mentions the following:
New synthetic methods for the catalytic functionalization of C-H bonds have the potential to revolutionize the synthesis of complex mols. However, the realization of this synthetic potential requires the ability to functionalize selectively one C-H bond in a compound containing many such bonds and an array of functional groups. The site-selective functionalization of aliphatic C-H bonds is one of the greatest challenges that must be met for C-H bond functionalization to be used widely in complex-mol. synthesis, and processes catalyzed by transition-metals provide the opportunity to control selectivity. Current methods for catalytic, aliphatic C-H bond functionalization typically rely on the presence of one inherently reactive C-H bond, or on installation and subsequent removal of directing groups that are not components of the desired mol. To overcome these limitations, we sought catalysts and reagents that would facilitate aliphatic C-H bond functionalization at a single site, with chemoselectivity derived from the properties of the catalyst and site-selectivity directed by common functional groups contained in both the reactant and the desired product. Here, we show that the combination of an iridium-phenanthroline catalyst and a dihydridosilane reagent leads to the site-selective γ-functionalization of primary C-H bonds controlled by a hydroxyl group, the most common functional group in natural products. The scope of the reaction encompasses alcs. and ketones bearing many substitution patterns and auxiliary functional groups; this broad scope suggests that this methodol. will be suitable for the site-selective and diastereoselective functionalization of complex natural products. For example, treating (+)-fenchol with [Ir(cod)OMe]2 and Et2SiH gave the corresponding diethyl(hydrido)silyl ether, which was cyclized using [Ir(cod)OMe]2/Me4phen to give an intermediate oxasiloxane. The latter compound was oxidized under Tamao-Fleming conditions and then diacylated to give hydroxyfenchol diacetate I in 66% yield. In the experiment, the researchers used many compounds, for example, N,N-Diethyl-4-iodobenzamide (cas: 77350-52-8Application In Synthesis of N,N-Diethyl-4-iodobenzamide).
N,N-Diethyl-4-iodobenzamide (cas: 77350-52-8) belongs to iodide derivatives. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. The C–I bond is the weakest of the carbon–halogen bonds. These bond strengths correlate with the electronegativity of the halogen, decreasing in the order F > Cl > Br > I. This periodic order also follows the atomic radius of halogens and the length of the carbon-halogen bond.Application In Synthesis of N,N-Diethyl-4-iodobenzamide
Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com