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 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.

6 Different Diversification Groups

 

baran_late_stage

Sulfinate Alkylation 6X Reagents (2 Vials of each)

2X6 Array

 

baran_production_kit_button
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 135 µl
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 13.5 µl

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 20.8 µl 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 in 0.210 ml selected solvent. 35 µl is added in each vial followed by 2.1 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.

Request Form

Interested in learning more about our products?
Complete our request form and we’ll get back to you as soon as possible.

photochemistry surprise
Photochemistry Surprises!!!

Featuring a project where “hey that’s weird & very wrong” turns into something fantastic: Bold decisions, stubbornness & ingenuity result in a new opportunity.

photochemistry 2022
A Photochemistry Year in Review 2022

Here is our list of the 22 photochemistry papers that we thought were the best, funniest, oddest, most interesting, or downright unexpected of 2022.

Lucent 360, photoredox, C-N couplings
Lucent360 Customized Reaction Screenings

Learn how to streamline with Lucent360 customized reaction screenings and save on time & setups when matching optimal wavelength to a photocatalyst.

Upcycling Plastic Using Light
Photocatalytic Deconstruction of Polystyrene

What if we could shine a blue LED on our 8 billion tons of plastic waste and get back a valuable chemical feedstock? Click to read about the Reisner group’s work looking at tackling this problem.

photocatalysis in seawater
Photocatalysis in Seawater

Seawater: It’s abundant, messy, contains salts, microorganisms, biomass, organic and inorganic pollutants (and microplastics) and might just be a great solvent for generating hydrogen peroxide with visible light photocatalysis

Comparing Commercial Photoreactors

How should we compare commercial photoreactors? Or better yet, how do we discuss the important details of a photochemical reaction?

The 21 Must-Read Photochemistry Papers of 2021

Beyond the best photochemistry papers of 2021, read about the amazing year we had here at HepatoChem.

Utilizing the Lucent360 From Screen to Scale

Read on for a step by step study taking a photocatalyzed-Arbuzov reaction from screen to scale utilizing the unique features of the Lucent360™

Introducing the Lucent360

The Lucent360’s flexible design gives you the best options to learn everything you need to know to take your photochemical reactions from screen to scale.

Photochemistry of earth-abundant metals

A recurring theme in our recent articles: there isn’t enough iridium or ruthenium in the earth’s crust to do all the photochemistry we’d like to do at scale.

The Attack of the Photocatalytic Microrobots!

Self-propelled autonomous microrobots that can swim through mazes to seek and destroy microplastics? Read on…

Stay up-to-date!
Get insights and tips from experts