Baran Alkylation-Sulfinate Alkylation Production Kit

Baran Alkylation kit:
Sulfinate Alkylation Production
(HCK1013-01-001)

 6 Different Diversification Groups

baran_late_stage

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 (HCK1013-01-002) and a production kit (HCK1013-01-001) to conveniently produce in one step 6 different analogues of a lead compound in 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.

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.

Prepare a solution of substrate with 300 µmol of substrate in 2.1 ml selected solvent.

  • Add 350 µl of substrate solution to each reagent vial containing the sulfinates. Shake the vial to allow reagents to mix properly.
  • If needed add 80 µl of H2O/TFA in each vial.
  • Add 21 µl of TBHP in each vial.
  • Stir the reaction vials in the reaction block at 50°C for 12-24 hours.
  • Remove the vial caps.
  • 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.

 

 

Sulfinate Alkylation Solvent Effect

 

hydroquinine

Substrate: Hydroquinine
DFES-solvent

 TFES-solvent

 

 DFMS-solvent

 

TFMS-solvent IPS-solvent
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