《Synthesis of Acyclic Aliphatic Amides with Contiguous Stereogenic Centers via Palladium-Catalyzed Enantio-, Chemo- and Diastereoselective Methylene C(sp3)-H arylation》 was written by Han, Ye-Qiang; Yang, Xu; Kong, Ke-Xin; Deng, Yao-Ting; Wu, Le-Song; Ding, Yi; Shi, Bing-Feng. Category: iodides-buliding-blocks And the article was included in Angewandte Chemie, International Edition in 2020. The article conveys some information:
The enantioselective desymmetrizing C-H activation of α-gem-dialkyl acyclic amides remains challenging because the availability of four chem. identical unbiased methylene C(sp3)-H bonds and increased rotational freedoms of the acyclic systems add tremendous difficulties for chemo- and stereocontrol. We have developed a method for the synthesis of acyclic aliphatic amides with α,β-contiguous stereogenic centers via PdII-catalyzed asym. arylation of unbiased methylene C(sp3)-H, in good yields and with high levels of enantio-, chemo- and diastereoselectivity [up to >99% ee and >20:1 d.r.; e.g., amide I + PhI → II (75%, > 20:1 d.r., 98% ee)]. Successive application of this method enables the sequential arylation of the gem-dialkyl groups with two different aryl iodides, giving a range of β-Ar1-β’-Ar2-aliphatic acyclic amides containing three contiguous stereogenic centers with excellent diastereoselectivity. In the experiment, the researchers used many compounds, for example, 3-Iodophenol(cas: 626-02-8Category: iodides-buliding-blocks)
3-Iodophenol(cas: 626-02-8) belongs to organic iodides. The carbon-iodine bond is weaker than other carbon-halogen bonds due to the poor electronegative nature of the iodine atom. Category: iodides-buliding-blocks Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.
Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com