Dibutylboron trifluoromethanesulfonate

Chemical Properties

clear light yellow to orange solution

Uses

Dibutylboryl trifluoromethanesulfonate may be used in the following studies:

• Stereo- and regio-selective synthesis of erythro aldols.
• As a promoter for the solution and polymer-supported trichloroacetimidate-based glycosylations.
• Synthesis of β-alkoxy carbonyl compounds via one-step Mukaiyama aldol-type reaction.
• Aldol-type cyclization for the stereoselective synthesis of cyclic ethers.
• As a reagent for the formation of boron enolates.
• As a complexation aid for the isolation of 1-acyldipyrromethanes.
• As a promoter in [1,2]-Wittig reaction between aldehydes and O-benzyl or O-allyl glycolate esters, creating two contiguous stereocenters (1,2-diol) in good yield without the need for strong base.

General Description

Dibutylboryl trifluoromethanesulfonate (Dibutylboron triflate, Bu₂BOTf) is an organometallic reagent. It efficiently promotes the1,4-addition of benzylic and allylic organocopper reagents.

Purification Methods

Distil it in a vacuum under argon and store it under argon. It should be used within 2 weeks of purchase or after redistillation. Use a short path distillation system. It has IR bands in CCl4 at max 1405, 1380, 1320, 1200 and 1550cm
1 , and 1 3C NMR (CDCl3) with at 118.1, 25.1, 21.5 and 13.6ppm. [Gage & Evans Org Synth 68 83 1990, Evans et al. J Am Chem Soc 103, 3099 1981.] TOXIC