138381-01-8Relevant articles and documents
Organoboranes. 41. Reaction of Organoboranes with (Dichloromethyl)lithium. Scope and Limitations. Synthesis of Homologated Primary and Secondary Alcohols
Brown, Herbert C.,Imai, Toshiro,Perumal, P. Thirumali,Singaram, Bakthan
, p. 4032 - 4036 (1985)
Homologated primary alcohols were prepared from alkylboronic esters by the reaction with (dichloromethyl)lithium, LiCHCl2, followed by KIPBH treatment and oxidation.Homologated secondary alcohols were prepared from representative dialkylborinic esters and trialkylboranes by the reaction with LiCHCl2, followed by treatment with base and oxidation.The yields are generally good with both boronic and borinic esters.On the other hand, the reactions with trialkylboranes exhibited a sensitivity to large steric requirements in the trialkylborane reactant.
Fe-Catalyzed Anaerobic Mukaiyama-Type Hydration of Alkenes using Nitroarenes
Bhunia, Anup,Bergander, Klaus,Daniliuc, Constantin Gabriel,Studer, Armido
supporting information, p. 8313 - 8320 (2021/03/08)
Hydration of alkenes using first row transition metals (Fe, Co, Mn) under oxygen atmosphere (Mukaiyama-type hydration) is highly practical for alkene functionalization in complex synthesis. Different hydration protocols have been developed, however, control of the stereoselectivity remains a challenge. Herein, highly diastereoselective Fe-catalyzed anaerobic Markovnikov-selective hydration of alkenes using nitroarenes as oxygenation reagents is reported. The nitro moiety is not well explored in radical chemistry and nitroarenes are known to suppress free radical processes. Our findings show the potential of cheap nitroarenes as oxygen donors in radical transformations. Secondary and tertiary alcohols were prepared with excellent Markovnikov-selectivity. The method features large functional group tolerance and is also applicable for late-stage chemical functionalization. The anaerobic protocol outperforms existing hydration methodology in terms of reaction efficiency and selectivity.
Radical addition of silanes to alkenes followed by oxidation
Palframan, Matthew J.,Parsons, Andrew F.,Johnson, Paul
scheme or table, p. 2811 - 2814 (2012/01/06)
Phenyldimethylsilane and trichlorosilane are shown to undergo efficient radical hydrosilylation reactions, on reaction with various alkenes, using triethylborane as the initiator. Adducts from the trichlorosilane reactions can be oxidised to afford alcohols in good yields. This two-step process leads to the anti-Markovnikov hydration of alkenes. Georg Thieme Verlag Stuttgart · New York.
