0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via S-Arylation Reactions

DOI: 10.1055/sos-SD-104-00490

Gagnon, A.; Benoit, E.; Le Roch, A.Science of Synthesis Knowledge Updates, (2018478.

Very few examples of S-arylation reactions using organobismuth reagents have been reported. The phenylation of a small number of arenethiols was performed in good to excellent yield using triphenylbismuth(V) carbonate;[‌310‌] however, because thiols have a propensity to form diaryl disulfides, S-arylation methods involving organobismuthines have been developed directly from diaryl disulfides. Thus, reaction of diaryl disulfides 168 with triarylbismuthines and copper(I) acetate in the presence of 1,10-phenanthroline in dimethyl sulfoxide at 100°C under air affords the corresponding diaryl thioethers 169 in good to excellent yields (Scheme 93).[‌347‌] Interestingly, and contrary to other copper-catalyzed arylation reactions using triarylbismuthines, more than one aryl group is transferred from the organobismuth reagent.

Meeeee 88 Meeeee(M) Meeeeee Meeeeeeee M-Meeeeeeee ee Meeeee Meeeeeeeee Meeee Meeeeeeeeeeeeeeeee[‌888‌]

Meeeeeeeeee 88

Me8 Me8 Meeee (%) Mee
Me 8-MeMM8M8 88 [‌888‌]
8-MeMM8M8 Me 88 [‌888‌]
Mee Me 88 [‌888‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeeeeeeeeee Meeeee Meeeeee (888, Me8 = Me; Me8 = 8-MeMM8M8); Meeeeee Meeeeeeee:[‌888‌]

M eeeeeee ee (8-MeMM8M8)8Me (888 ee, 8.8 eeee, 8.88 eeeee), eeeeeeee eeeeeeeee (888, Me8 = Me; 888 ee, 8.88 eeee), MeMMe (8.8 ee, 8.88 eeee, 8.888 eeeee), eee 8,88-eeeeeeeeeeeeee (8.8 ee, 8.88 eeee) ee MMMM (8 eM) eee eeeeee ee 888°M eee 8 e eeeee eee. Meeee eeeeeeee ee eee eeeeeee eeee MM8Me8 (88 eM) eee M8M (88 eM), eee eeeeee eeee eeeeeeeee, eee eee eeeeeee eeeee eee eeeeeeeee eeee MM8Me8 (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee 8% ee MM8 eee M8M, eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeee/MM8Me8 8:8); eeeee: 88%.