Huang, Qiang; Su, Yu-Xuan; Sun, Wei; Hu, Meng-Yang; Wang, Wei-Na; Zhu, Shou-Fei published the artcile< Iron-Catalyzed Vinylzincation of Terminal Alkynes>, Computed Properties of 10602-04-7, the main research area is iron complex containing tridentate phenanthrolineimine ligand preparation catalyst vinylzincation; crystal structure iron complex containing tridentate phenanthrolineimine ligand; terminal alkyne vinylation vinylzincation iron phenanthrolineimine catalyst.
Organozinc reagents are among the most commonly used organometallic reagents in modern synthetic chem., and multifunctionalized organozinc reagents can be synthesized from structurally simple, readily available ones by alkyne carbozincation. However, this method suffers from poor tolerance for terminal alkynes, and transformation of the newly introduced organic groups is difficult, which limits its applications. Herein, the authors report a method for vinylzincation of terminal alkynes catalyzed by newly developed Fe catalysts bearing 1,10-phenanthroline-imine ligands. This method provides efficient access to novel organozinc reagents with a diverse array of structures and functional groups from readily available vinylzinc reagents and terminal alkynes. The method features excellent functional group tolerance (tolerated functional groups include amino, amide, cyano, ester, hydroxyl, sulfonyl, acetal, phosphono, pyridyl), a good substrate scope (suitable terminal alkynes include aryl, alkenyl, and alkyl acetylenes bearing various functional groups), and high chemoselectivity, regioselectivity, and stereoselectivity. The method could significantly improve the synthetic efficiency of various important bioactive mols., including vitamin A. Mechanistic studies indicate that the new Fe-1,10-phenanthroline-imine catalysts developed in this study has an extremely crowded reaction pocket, which promotes efficient transfer of the vinyl group to the alkynes, disfavors substitution reactions between the Zn reagent and the terminal C-H bond of the alkynes, and prevents the further reactions of the products. The authors’ findings show that Fe catalysts can be superior to other metal catalysts in terms of activity, chemoselectivity, regioselectivity, and stereoselectivity when suitable ligands were used.
Journal of the American Chemical Society published new progress about Alkadienes Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 10602-04-7 belongs to class alcohols-buliding-blocks, and the molecular formula is C9H8O, Computed Properties of 10602-04-7.
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts