4516-10-3Relevant articles and documents
Cobalt-Catalyzed Kumada Coupling Forming Sterically Encumbered C-C Bonds
Brennan, Marshall R.,Darrow, William T.,Fout, Alison R.,Killion, Jack A.,Leahy, Clare A.
, (2021/12/02)
A Co(acac)3/PN precatalyst was developed and optimized for catalytic Kumada coupling of aryl Grignard reagents to sterically encumbered alkyl halides. The substrate scope demonstrates excellent yields for primary alkyl chlorides and bromides, including good performance using neopentyl chloride and neophyl chloride. Secondary alkyl halides were also successfully arylated in good yields, and the presence of β-hydrogen atoms in a substrate did not inhibit product formation. An intermolecular functional group tolerance screen was conducted which indicates that ester and amide functionality are well tolerated by the reaction conditions. Electrophiles containing ester, pyridine, and nitrile functionality were all coupled with 2-mesitylmagnesium bromide in good yields, supporting tolerance screen results. The intermolecular screen also showed that functional groups which are typically reactive with Grignard reagents such as alcohols and terminal alkynes were not well-tolerated by the reaction.
Sterically congested phosphonium borate acids as effective Br?nsted acid catalysts
Sinha, Arup,Jaiswal, Amit K.,Young, Rowan D.
, p. 36 - 43 (2016/12/06)
Phosphonium borate acids [HPPh2(C6F5)][B(C6F5)4] (2), [HPMes2(C6F5)][B(C6F5)4] (3) and [HPMes(C6F5)2][B(C6F5)4] (4) were synthesized via heterolytic dihydrogen cleavage in the presence of triisopropylsilylium and characterized by spectroscopic and crystallographic methods. Br?nsted acid catalysis using compounds 2–4 proved to be efficient for a number of challenging reactions (namely ionic hydrogenation, hydroamination and hydroarylation), owing to the restrained nucleophilicity of the sterically hindered conjugate bases. Reactivity of compounds 2–4 suggests that their pKavalues are similar to that of diethyl oxonium acid.
Microporous acidic cesium salt of 12-tungstosilicic acid Cs 3HSiW12O40 as a size-selective solid acid catalyst
Kamiya, Yuichi,Sano, Shogo,Miura, Yu-Ki,Uchida, Yohei,Ogawa, Yuki,Iwase, Yukari,Okuhara, Toshio,Degnan Jr.
supporting information; scheme or table, p. 881 - 883 (2011/01/08)
An acidic Cs salt of H4SiW12O4O 40 (Cs3HSiW12O40), which was prepared by titrating an aqueous solution of H4SiW12O 40 with an aqueous solution of Cs2CO3, possessed only micropores and exhibited size-selective catalysis for acid-catalyzed reactions in liquid phase.