Sodium Aminodiboranate, a New Reagent for Chemoselective Reduction of Aldehydes and Ketones to Alcohols
Sodium aminodiboranate (NaNH 2(BH 3) 2, NaADBH) is a new member of the old borane family, which exhibits superior performance in chemoselective reduction. Experimental results show that NaADBH can rapidly reduce aldehydes and ketones to the corresponding alcohols in high efficiency and selectivity under mild conditions. There are little steric and electronic effects on this reduction.
Wang, Jin,Guo, Yu,Li, Shouhu,Chen, Xuenian
supporting information
p. 1104 - 1108
(2021/05/25)
Aliphatic thioethers by s-alkylation of thiols via trialkyl borates
A simple and convenient one-pot procedure is described for the synthesis of thioethers via boron esters. This procedure involves in-situ generation of alkyl sulfates by reaction of trialkyl borates with concentrated sulfuric acid and subsequent reaction with thiols in the presence of pyridine. The reactions with boron esters of primary or secondary alcohols proceed cleanly at 100C and afford aliphatic thioethers in reasonable yields (59-93%) within 24 h. Interestingly, the 1H NMR spectra of the products showed no sign of positional isomerisms. The method fails however with thiophenol and does not yield aromatic thioethers, due to electrophilic substitution at the phenyl ring. Copyright Taylor & Francis Group, LLC.
Gunes, Deniz,Sirkecioglu, Okan,Bicak, Niyazi
body text
p. 1685 - 1690
(2010/09/17)
Practical and efficient procedure for the in situ preparation of B-alkoxyoxazaborolidines. Enantioselective reduction of prochiral ketones
A new method for the in situ elaboration of B-alkoxyoxazaborolidines is presented. Their use in the enantioselective reduction of prochiral aromatic ketones provides excellent chemical and optical yields of chiral alcohols.
Ponzo, Viviana L.,Kaufman, Teodoro S.
p. 495 - 496
(2007/10/03)
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