ZrCl₄/NaI and ZrOCl₂ · 8H₂O/NaI as effective systems for reductive coupling of sulfonyl chlorides and chemoselective deoxygenation of sulfoxides

Abstract

Zirconium tetrachloride/sodium iodide (ZrCl 4 /NaI) and ZrOCl 2 · 8H 2 O/NaI conduct effective reductive coupling of sulfonyl chlorides to their corresponding disulfides and chemoselective reduction of sulfoxides to their thioethers in high yields.

Some applications of zirconium(IV) tetrachloride (ZrCl4) and zirconium(IV) oxydichloride octahydrate (ZrOCl2.8H2O) as catalysts or reagents in organic synthesis

“…The use of zirconium tetrachloride/sodium iodide (ZrCl 4 /NaI) and ZrOCl 2 .8H 2 O/NaI for effective reductive coupling of sulfonyl chlorides to their corresponding disulfides and chemoselective reduction of sulfoxides to their thioethers in high yields have been also reported (Scheme 7) [13].…”

Applications of Zirconium (IV) Compounds in Organic Synthesis

“…Firouzabadi and co-workers reported the use of ZrCl 4 /NaI and ZrOCl 2 ·8H 2 O/NaI as efficient systems for reductive couping sulfonyl chlorides to their symmetric disulfides and chemoselective deoxygenation of sulfoxides to the related thioethers (Scheme 25) [68]. The symmetric disulfides 65 were obtained in 88-95% yields.…”

ZrOCl2·8H2O/silica gel as a new efficient and a highly water–tolerant catalyst system for facile condensation of indoles with carbonyl compounds under solvent-free conditions

“…Solvent-free condensation of indoles with carbonyl compounds is scarce in the literature [14]. Along this line and in continuation of our interest to explore new applications of Zr(IV) compounds [18][19][20][21][22][23][24], we now introduce ZrOCl 2 ·8H 2 O/silica gel as a new efficient catalytic system for carbon-carbon bond formation between indoles and carbonyl compounds under solvent-free conditions in good to high yields (Scheme 1). ZrOCl 2 ·8H 2 O is a highly water-tolerant compound, which its handling does not need especial precautions.…”