In 2016,del Aguila-Sanchez, Miguel A.; Navarro, Yolanda; Garcia Lopez, Jesus; Guedes, Guilherme P.; Lopez Ortiz, Fernando published 《Synthesis of P-stereogenic diarylphosphinic amides by directed lithiation: transformation into tertiary phosphine oxides via methanolysis, aryne chemistry and complexation behaviour toward zinc(II)》.Dalton Transactions published the findings.Name: 1,2-Diiodoethane The information in the text is summarized as follows:
The highly diastereoselective synthesis of P-stereogenic phosphinic amides via directed ortho lithiation (DoLi) of (SC)-P,P-diphenylphosphinic amides with t-BuLi followed by electrophilic quench reactions is described. Functionalized derivatives containing a wide variety of ortho substituents (Cl, Br, I, OH, N3, SiMe3, SnMe3, P(O)Ph2, Me, allyl, tBuOCO) have been prepared in high yields with diastereomeric ratios up to 98:2. The X-ray diffraction structure of the ortho-stannylated and ortho-iodo compounds showed that the pro-S P-Ph ring was stereoselectively ortho-deprotonated by the organolithium base. The usefulness of the method is supported by two key transformations, the synthesis of P-stereogenic Me phosphinates through replacement of the chiral auxiliary by a methoxy group and the first example of the insertion of benzyne into the P-N bond of a P-stereogenic phosphinic amide. A DFT study of this reaction showed that the insertion proceeds through a [2+2] cycloaddition and a subsequent ring-opening with retention of the P-configuration. Explorative coordination chem. of the new P-stereogenic ligands provided access to a chiral phosphinic amide-phosphine oxide Zn(II) complex, the crystal structure of which is reported.1,2-Diiodoethane(cas: 624-73-7Name: 1,2-Diiodoethane) was used in this study.
1,2-Diiodoethane(cas: 624-73-7) is one of organic iodides. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond. Iodo alkanes participate in a variety of organic synthesis reactions, which include the SimmonsSmith reaction (cyclopropanation using iodomethane), Williamson ether synthesis, Wittig reaction, Grignard reaction, alkyl coupling reactions, and Wurtz reaction.Name: 1,2-Diiodoethane
Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com