18737-73-0Relevant articles and documents
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.
A useful, reliable and safer protocol for hydrogenation and the hydrogenolysis of o-benzyl groups: The in situ preparation of an active Pd 0/C catalyst with well-defined properties
Felpin, Francois-Xavier,Fouquet, Eric
supporting information; experimental part, p. 12440 - 12445 (2011/01/05)
A simple, highly reproducible protocol for the hydrogenation of alkenes and alkynes and for the hydrogenolysis of O-benzyl ethers has been developed. The method features the in situ preparation of an active Pd0/C catalyst from Pd(OAc)2 and charcoal, in methanol. The mild reaction conditions (25°C) and low catalyst loading required (0.025 mol%), as well as the absence of contamination of the product by palladium residues (0/C: It's a kind of magic! A sustainable, simple and highly reproducible protocol for the hydrogenation of alkenes and alkynes (see scheme) and for the hydrogenolysis of O-benzyl ethers has been developed with an in situ generated Pd0/C catalyst. The homemade Pd0/C catalyst allows mild reaction conditions (25°C, 1 atm H2) and low catalyst loading (as low as 0.025 mol%), without any contamination of the product by palladium residues (4 ppb).
Tandem reaction by using compatible catalysts: Cross-metathesis reaction and hydrogenation
Cossy, Janine,Bargiggia, Frédéric C.,BouzBouz, Samir
, p. 6715 - 6717 (2007/10/03)
A one-pot tandem cross-metathesis/hydrogenation procedure was achieved at room temperature, under one atmosphere of hydrogen, in the presence of ruthenium catalyst II and PtO2 showing the compatibility of the two catalysts.
