Sulfinate Alkylation Reagent Kit


Sulfinate Alkylation Diversification Kits:
HCK1013-01-001
HCK1013-01-002

Product overview:

 

The sulfinate alkylation reaction described by Prof. Baran is a powerful late stage functionalization tool. Our kit is available in 2 sizes. A small scale kit to screen the chemistry using multiple solvents and a production kit to conveniently produce in one step 6 different analogues of a lead compoundin mg quantities. Each reaction vial contains sulfinate alkylation reagent (pre-weighed) and a stirring bar to react with your substrate. C-H functionalization will primarily occur on electron-deficient heteroarenes at one or several positions.
6 Different Diversification Groups

 

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Sulfinate Alkylation 6X Reagents (2 Vials of each)

2X6 Array

 
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HCK1013-01-001
HCK1013-01-002
Quantity
Reagents
Amount
2x DFMS-Zn 100 μmol
2x TFMS-Zn 100 μmol
2x DFES-Na 100 μmol
2x TFES-Zn 100 μmol
2x IPS-Zn 100 μmol
2x TFPS-Na 100 μmol
2x TBHP 135μl
Quantity
Reagents
Amount
2x DFMS-Zn 10 μmol
2x TFMS-Zn 10 μmol
2x DFES-Na 10 μmol
2x TFES-Zn 10 μmol
2x IPS-Zn 10 μmol
2x TFPS-Na 10 μmol
2x TBHP 13.5μl

Standard Protocol:

Several solvents or solvent mixtures can be used to perform the reaction (DMSO, DMSO/H2O/TFA, CHCl3/H2O/TFA… ). A solution of substrate is made with 300 μmol of substrate in 2.1 ml selected solvent. 350 μl is added in each vial followed by 20.8μl of TBuOOH (70% in water). The reactions are allowed to stir at 50°C for 12-24 hours.

 

Standard Protocol:

Several solvents or solvent mixtures can be used to perform the reaction (DMSO, DMSO/H2O/TFA, CHCl3/H2O/TFA… ). A solution of substrate is made with 30 μmol of substrate in0.210 ml selected solvent. 35 μl is added in each vial followed by2.1 μl of TBuOOH (70% in water). The reactions are allowed to stir at 50°C for 12-24 hours.

 

 

Sulfinate Alkylation Reagents (2 Vials of each)
Zinc difluoro methane sulfinate Zinc trifluoro methane sulfinate Sodium
1,1-difluoro ethane sulfinate		 Zinc trifluoro ethane sulfinate Zinc isopropyl sulfinate Sodium trifluoro propyl sulfinate
ZnDFMS ZnTFMS NaDFES ZnTFES ZnIPS NaTFPS
MW (g/mol) 295.55 331.53 152.10 359.58 279.69 184.11
CAS Number 1355729-38-2 39971-65-8 1422738-67-7 1416821-53-8 1416821-55-0 1263377-91-8

 

Sulfinate Alkylation Solvent Effect

hydroquinine

Substrate: Hydroquinine
 DFES-solvent

TFES-solvent

 

DFMS-solvent

 
TFMS-solvent IPS-solvent

 

 

 

HCK1013-01-001

The typical protocol is performed at 0.142 mol/l concentration reaction condition. 2 equivalents of sulfinate reagent are preloaded (100 μmol) and 3 equivalents of TBHP is added. These reaction conditions are not air sensitive.

Recommended solvents are DMSO or CHCl3 with or without H2O/TFA (0.1 ml of TFA in 2 ml of water). H2O/TFA can change the regioselectivity and conversion of the reaction.

  1. Prepare a solution of substrate with 300 μmol of substrate in 2.1 ml selected solvent.
  2. Add 350 μl of substrate solution to each reagent vial containing the sulfinates. Shake the vial to allow reagents to mix properly.
  3. If needed add 80 μl of H2O/TFA in each vial.
  4. Add 21 μl of TBHP in each vial.
  5. Stir the reaction vials in the reaction block at 50°C for 12-24 hours.
  6. Remove the vial caps.
  7. Prepare analytical sample for each reaction condition with 5 μl sample diluted into 200 μl in either DMSO or water/acetonitrile 50/50.

Analyze resulting analytical samples by LC/MS.

 

 

 

HCK1013-01-002

The typical protocol is performed at 0.142 mol/l concentration reaction condition. 2 equivalents of sulfinate reagent are preloaded (10 μmol) and 3 equivalents of TBHP is added. These reaction conditions are not air sensitive.

Recommended solvents are DMSO or CHCl3 with or without H2O/TFA (0.1 ml of TFA in 2 ml of water). H2O/TFA can change the regioselectivity and conversion of the reaction.

  1. Prepare a solution of substrate with 30 μmol of substrate in 210 μl selected solvent.
  2. Add 35 μl of substrate solution to each reagent vial containing the sulfinates. Shake the vial to allow reagents to mix properly.
  3. If needed add 8 μl of H2O/TFA in each vial.
  4. Add 2.1 μl of TBHP in each vial.
  5. Stir the reaction vials in the reaction block at 50°C for 12-24 hours.
  6. Remove the vial caps.
  7. Prepare analytical sample for each reaction condition with 5 μl sample diluted into 200 μl in either DMSO or water/acetonitrile 50/50.

Analyze resulting analytical samples by LC/MS.

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