Dibutylboryl trifluoromethanesulfonate solution

Name: Dibutylboryl trifluoromethanesulfonate solution
Brand: ALDRICH

1.0 M in methylene chloride

Synonym(s):

Dibutylboron triflate solution

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About This Item

Linear Formula:

CF₃SO₃B[(CH₂)₃CH₃]₂

CAS Number:

60669-69-4

Molecular Weight:

274.11

UNSPSC Code:

12352106

NACRES:

NA.22

PubChem Substance ID:

24855812

MDL number:

MFCD00009669

Beilstein/REAXYS Number:

1968660

Form:

liquid

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Properties

form

liquid

concentration

1.0 M in methylene chloride

density

1.271 g/mL at 25 °C

SMILES string

CCCCB(CCCC)OS(=O)(=O)C(F)(F)F

InChI

1S/C9H18BF3O3S/c1-3-5-7-10(8-6-4-2)16-17(14,15)9(11,12)13/h3-8H2,1-2H3

InChI key

FAVAVMFXAKZTMV-UHFFFAOYSA-N

Description

General description

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

Application

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.