96346-16-6Relevant articles and documents
Iron-Catalyzed Highly Enantioselective Hydrogenation of Alkenes
Lu, Dongpo,Lu, Peng,Lu, Zhan,Ren, Xiang,Sun, Yufeng,Xu, Haofeng
supporting information, p. 12433 - 12438 (2021/08/23)
Here, we reported for the first time an iron-catalyzed highly enantioselective hydrogenation of minimally functionalized 1,1-disubstituted alkenes to access chiral alkanes with full conversion and excellent ee. A novel chiral 8-oxazoline iminoquinoline ligand and its iron complex have been designed and synthesized. This protocol is operationally simple by using 1 atm of hydrogen gas and shows good functional group tolerance. A primary mechanism has been proposed by the deuterium-labeling experiments.
Catalytic protodeboronation of pinacol boronic esters: Formal anti-Markovnikov hydromethylation of alkenes
Clausen, Florian,Kischkewitz, Marvin,Bergander, Klaus,Studer, Armido
, p. 6210 - 6214 (2019/06/27)
Pinacol boronic esters are highly valuable building blocks in organic synthesis. In contrast to the many protocols available on the functionalizing deboronation of alkyl boronic esters, protodeboronation is not well developed. Herein we report catalytic protodeboronation of 1°, 2° and 3° alkyl boronic esters utilizing a radical approach. Paired with a Matteson-CH2-homologation, our protocol allows for formal anti-Markovnikov alkene hydromethylation, a valuable but unknown transformation. The hydromethylation sequence was applied to methoxy protected (-)-Δ8-THC and cholesterol. The protodeboronation was further used in the formal total synthesis of δ-(R)-coniceine and indolizidine 209B.
Indium(III) triflate - A catalyst for greener aromatic alkylation reactions
Mack, Ryan,Askins, Grant,Lowry, Jacob,Hurley, Nathan,Reeves, Perry C.
, p. 1262 - 1265 (2014/01/06)
An environmentally friendly method for alkylating aromatic compounds with simple alcohols in the presence of a catalytic amount of indium(III) triflate is reported. Ionic liquids are used as solvents and energy-efficient heating is provided by microwave radiation. Good yields are obtained with benzyl, secondary, and tertiary alcohols. Simple primary alcohols are not effective alkylating agents under these conditions. With tertiary alcohols, activated aromatic compounds such as toluene and anisole must be used to obtain good yields. The catalyst, which is immobilized in a water-insoluble ionic liquid, can be easily recycled without significant loss of activity.