13540-76-6Relevant articles and documents
Solvent Effects on Ipso versus Ortho Selectivity in the Reductive Iodonio-Claisen Rearrangement of Allenyl(p-methoxyphenyl)iodane
Ochiai, Masahito,Ito, Takao
, p. 2274 - 2275 (1995)
-
Iron-Catalyzed Vinylzincation of Terminal Alkynes
Huang, Qiang,Su, Yu-Xuan,Sun, Wei,Hu, Meng-Yang,Wang, Wei-Na,Zhu, Shou-Fei
supporting information, p. 515 - 526 (2022/01/08)
Organozinc reagents are among the most commonly used organometallic reagents in modern synthetic chemistry, and multifunctionalized organozinc reagents can be synthesized from structurally simple, readily available ones by means of 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, we report a method for vinylzincation of terminal alkynes catalyzed by newly developed iron 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 molecules, including vitamin A. Mechanistic studies indicate that the new iron-1,10-phenanthroline-imine catalysts developed in this study have an extremely crowded reaction pocket, which promotes efficient transfer of the vinyl group to the alkynes, disfavors substitution reactions between the zinc reagent and the terminal C–H bond of the alkynes, and prevents the further reactions of the products. Our findings show that iron catalysts can be superior to other metal catalysts in terms of activity, chemoselectivity, regioselectivity, and stereoselectivity when suitable ligands are used.
Ruthenium-Catalyzed Propargylic Reduction of Propargylic Alcohols with Hantzsch Ester
Ding, Haowei,Sakata, Ken,Kuriyama, Shogo,Nishibayashi, Yoshiaki
supporting information, p. 2130 - 2134 (2020/06/08)
Ruthenium-catalyzed propargylic reduction of propargylic alcohols bearing a terminal alkyne moiety is accomplished by using Hantzsch ester as a nucleophilic hydride source. A variety of secondary and tertiary propargylic alcohols are reduced to the corresponding propargylic reduced products such as 1-alkynes in excellent yields. Some mechanistic studies indicate that ruthenium-allenylidene complexes may work as key reactive intermediates.
HISTONE DEMENTHYLASE INHIBITORS
-
Paragraph 00175, (2014/10/18)
The present invention relates generally to compositions and methods for treating cancer and neoplastic disease. Provided herein are substituted pyrrolopyridine derivative compounds and pharmaceutical compositions comprising said compounds. The subject com