Odorless Reagent for the Introduction of S-tert-Butyl Group

2-(tert-Butyl)isothiouronium Bromide (1) is an odorless solid utilized as a reagent to introduce the tert-butylthio group. For instance, introduction of the tert-butylthio group proceeds by treating 1 with arylhlides in high yields in the presence of palladium catalyst.¹⁾ In addition, the tert-butyl group can be removed by treating with Brønsted acid or Lewis acid and a thioketal like 2 is afforded in the presence of acetone. On the other hand, by adding a catalytic amount of base, 1 can introduce the tert-butylthio group to ethyl bromoacetate.²⁾

Related Products

B6315

2-(tert-Butyl)isothiouronium Bromide

T2184

Tris(dibenzylideneacetone)dipalladium(0) (= Pd₂(dba)₃)

T0519

Triphenylphosphine (= PPh₃)

P1008

Potassium tert-Butoxide (= KOtBu)

T1663

Scandium(III) Triflate (= Sc(OTf)₃)

S0547

Sodium Ethoxide (= EtONa)

References

• 1) Improved, Odorless Access to Benzo[1,2-d;4,5-d']-bis[1,3]dithioles and Tert-butyl Arylsulfides via C-S Cross Coupling
  • K. Kopp, O. Schiemann, N. Fleck, Molecules 2020, 25, 3666.
• 2) Decomposition of S-alkylisothiouronium salts under anhydrous conditions - application to a facile preparation of nonsymmetrical dialkyl sulfides
  • F. A. Luzzio, Synth. Comm. 1984, 14, 209.

Page Top