Copper(I)‐Mediated Direct Trifluoromethylthiolation of Allylic Halides with Elemental Sulfur and (Trifluoromethyl)trimethylsilane

Abstract

A new method has been developed for the copper‐mediated trifluoromethylthiolation of allylic halides by using potassium fluoride, elemental sulfur, and (trifluoromethyl)trimethylsilane in anhydrous N,N‐dimethylformamide. This protocol provides facile access to a variety of allylic trifluoromethyl thioethers in moderate to good yields under mild, ligand‐free reaction conditions.

Synthesis of Alpha‐trifluoromethylthio Carbonyl Compounds: A Survey of the Methods for the Direct Introduction of the SCF3 Group on to Organic Molecules

“…[23] Compoundsb earing electron donatings ubstituents gave higher yields than those featuring electron withdrawing groups,b ut no product formationw as observed when ochloro and p-nitro groups were presento nt he aromatic ring. [23] Compoundsb earing electron donatings ubstituents gave higher yields than those featuring electron withdrawing groups,b ut no product formationw as observed when ochloro and p-nitro groups were presento nt he aromatic ring.…”

“…One year later,R en and Zeng reported ac opper(I)-catalyzed a-trifluoromethylthiolation of both aromatica nd aliphatic abromo ketones with elemental sulfur andC F 3 SiMe 3 performed in the absence of ligand (Scheme 13). [23] Compoundsb earing electron donatings ubstituents gave higher yields than those featuring electron withdrawing groups,b ut no product formationw as observed when ochloro and p-nitro groups were presento nt he aromatic ring.…”

Recent Advances in Organic Reactions Involving Elemental Sulfur

“…These ligand‐free conditions could also be applied successfully to allylic chlorides 525 to provide a variety of allyl sulfides 526 in moderate to good yields (Scheme ) …”