14289-62-4Relevant articles and documents
Template-Assisted meta-C?H Alkylation and Alkenylation of Arenes
Bag, Sukdev,Jayarajan, Ramasamy,Mondal, Rahul,Maiti, Debabrata
, p. 3182 - 3186 (2017)
To expand the scope of meta-functionalization, a pyrimidine-based template effective for the formation of β-aryl aldehydes and ketones, using allyl alcohols, by meta-C?H activation of benzylsulfonyl esters is described. In addition, α,β-unsaturated aldehydes were generated by in situ olefination and deprotection of allyl benzyl ethers. These new functionalizations at the meta-position of an arene have also been successfully implemented in benzylphosphonate, phenethyl carbonyl, and phenethylsulfonyl ester scaffolds. Key to these successful new functionalizations is the creation of an electropositive palladium center by accepting the electron cloud from the metal to the energetically low-lying π-orbitals of pyrimidine ring, and it favors coordination of allyl alcohol to the metal center.
Simple and efficient method for the protection of hydroxyl groups as 4-methoxybenzyl ethers
Kasprzycka, Anna,Ptaszek-Budniok, Agata,Szeja, Wies?aw
supporting information, p. 2276 - 2284 (2014/07/07)
PMB ethers of alcohols are obtained in good yields and under mild conditions using the 4-methoxybenzyl N-allyl thiocarbamate and N-bromosuccinimide (NBS)/TfOH as the catalyst. The present method is very fast, simple, and efficient. Copyright
Vinyl polymerization versus [1,3] O to C rearrangement in the ruthenium-catalyzed reactions of vinyl ethers with hydrosilanes
Harada, Nari-Aki,Nishikata, Takashi,Nagashima, Hideo
supporting information; experimental part, p. 3243 - 3252 (2012/06/01)
Two reactions, vinyl polymerization and [1,3] O to C rearrangement of vinyl ethers, are investigated in the ruthenium-catalyzed reaction with hydrosilanes. The reaction pathways are dependent on the substituents of the vinyl ether, in particular, those of the alkoxy group. Primary-, secondary-, and tertiary-alkyl vinyl ethers, ROCHCH2, are polymerized with ease to give the corresponding polymer in good yields. When R is electron-donating benzyl groups, the reaction does not give the polyvinyl ether but results in [1,3] O to C rearrangement to give the corresponding aldehyde, RCH2CHO in moderate to good yields. The rearrangement selectively proceeds when vinyl ethers having α-substituents are used as the starting materials to give the corresponding ketones in high yields. With catalytic amounts of hydrosilanes, the rearrangement gives ketones or aldehydes selectively. In sharp contrast, use of excess amounts of hydrosilanes leads to the rearrangement followed by reduction of the formed carbonyl group to give the corresponding silyl ethers in good yields. Nature of catalytically active species is discussed. Crown Copyright
