261475
Dibutylboryl trifluoromethanesulfonate solution
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:
Molecular Weight:
274.11
Beilstein:
1968660
MDL number:
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
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
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General description
Dibutylboryl trifluoromethanesulfonate (Dibutylboron triflate, Bu2BOTf) is an organometallic reagent. It efficiently promotes the1,4-addition of benzylic and allylic organocopper reagents.[1]
Application
Dibutylboryl trifluoromethanesulfonate may be used in the following studies:
- Stereo- and regio-selective synthesis of erythro aldols.[2]
- As a promoter for the solution and polymer-supported trichloroacetimidate-based glycosylations.[1]
- Synthesis of β-alkoxy carbonyl compounds via one-step Mukaiyama aldol-type reaction.[3]
- Aldol-type cyclization for the stereoselective synthesis of cyclic ethers.[4]
- As a reagent for the formation of boron enolates.[5]
- As a complexation aid for the isolation of 1-acyldipyrromethanes.[6]
- 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.[7]
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Carc. 2 - Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1B - STOT SE 3
Target Organs
Central nervous system
Storage Class Code
3 - Flammable liquids
WGK
WGK 3
Flash Point(F)
80.6 °F - closed cup
Flash Point(C)
27 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Synlett, 81-81 (1992)
Dibutylboron triflate promoted conjugate addition of benzylic and allylic organocopper reagents to chiral α,β-unsaturated N-acyl imidazolidinones.
van Heerden PS, et al.
Tetrahedron Letters, 37(39), 6985-6988 (1996)
Myra Beaudoin Bertrand et al.
Organic letters, 8(20), 4661-4663 (2006-09-22)
A new tandem Wittig Rearrangement/aldol reaction of O-benzyl or O-allyl glycolate esters is described. This reaction generates two carbon-carbon bonds and two contiguous stereocenters in a single step from simple starting materials. The [1,2]-Wittig rearrangement proceeds under very mild reaction
Lian-Sheng Li et al.
Organic letters, 6(1), 127-130 (2004-01-03)
one-step Mukaiyama aldol type reaction [reaction: see text] A highly efficient one-step Mukaiyama aldol-type reaction has been developed for the synthesis of beta-alkoxy carbonyl compounds starting from ketones and acetals/ketals. The reaction is mediated by a combination of Bu(2)BOTf and
Stereo-and regio-controlled aldol synthesis.
Kuwajima I, et al.
Tetrahedron Letters, 21(44), 4291-4294 (1980)
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