53317-13-8Relevant articles and documents
Levy,Schwartz
, p. 2201,2203 (1976)
A simple and efficient copper oxide-catalyzed Barbier-Grignard reaction of unactivated aryl or alkyl bromides with ester
Gao, Fei,Deng, Xiang-Jun,Tang, Yu,Tang, Jin-Peng,Yang, Jun,Zhang, Yuan-Ming
supporting information, p. 880 - 883 (2014/02/14)
An efficient one-pot route to synthesize tertiary alcohol compounds using Barbier-Grignard reaction of unactivated alkyl or aryl bromides with ester in THF at 65 C catalyzed by CuO has been developed and systematically investigated. A wide range of substituted tertiary alcohol compounds were obtained in good to high yields. The reaction is highly chemoselective. The mechanism involving the leaving group of R2O-group is discussed.
Hydroboration. 79. Preparation and Properties of Methylborane and Dimethylborane and Their Characteristics as Hydroborating Agents. Synthesis of Tertiary Alcohols Containing Methyl Groups via Hydroboration.
Brown, Herbert C.,Cole, Thomas E.,Srebnik, Morris,Kim, Kee-Won
, p. 4925 - 4930 (2007/10/02)
Lithium methylborohydride and lithium dimethylborohydride are readily prepared from the corresponding boronic and borinic esters.Methylborane and dimethylborane are cleanly liberated from these borohydrides by protonation with hydrogen chloride in ether, thus permitting the ready liberation of these methylboranes from the stable methylborohydrides.In contrast to the earlier gas-phase studies, methylborane in solution is remarkably stable to disproportionation, forming a strong dimer complex.However, dimethylborane in solution is less stable, undergoing some disproportionation at room temperature.By liberating these boranes in appropriate solvents in the presence of the alkenes, the redistribution can be controlled and a satisfactory preparation of dialkylmethylboranes achieved.These organoboranes can be carbonylated-oxidized to form the corresponding tertiary alcohols containing one or two methyl groups, the first time these valuable derivatives have been available via hydroboration.Gas chromatographic examination of these tertiary alcohols established the absence of significant redistribution.The regioselectivity of these two new hydroborating agents was investigated with representative alkenes, and excellent selectivities with terminal and trisubstituted alkenes were achieved.
