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 Miscellaneous Reactions

DOI: 10.1055/sos-SD-120-00188

Cellnik, T.; Jo, W.; Healy, A.Science of Synthesis Knowledge Updatesearly view.

Tricyclohexylsilaneselenol (168) can be coupled with aryl halides in the presence of a catalyst formed from palladium(II) acetate and 2-(dicyclohexylphosphino)-2,6-diisopropoxybiphenyl (RuPhos; Scheme 63). Aryl chlorides are incompatible with this procedure, but aryl bromides and iodides are efficiently converted into selenoacetates 169 at room temperature by treatment of the tricyclohexyl-protected areneselenol intermediates with tetrabutylammonium fluoride and acetyl chloride. Exceptions to this general trend are substrates possessing a nitro group or an enolizable carbonyl moiety.[‌277‌]

Meeeee 88 Meeeeeeee ee Me-Meee Meeeeeeeeeeeee eeee Meee Meeeeeee[‌888‌]

Meeeeeeeeee 88

Me8 Meeee (%) Mee
Me 88 [‌888‌]
8-MeMM8M8 88 [‌888‌]
8-MM8M8 88 [‌888‌]
8-Me8MM8M8 88 [‌888‌]
8-MeM8M8 88 [‌888‌]
88 [‌888‌]

Meeeeeeeeeee Meeeeeeee

Me-Meee Meeeeeeeeeeeee 888; Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeeee eeeeeeeeeeeeeeeeeeee ee e eeeeee eeeeeeeee eeeeee. Me eee ee eeeee ee eeeeeeeee ee eeeeee eeeeeee. Me eeeeee eeeee eeee eeeee ee eee eeeeee.

M 8 M eeee ee MeMMMM ee MMM (8.8 eeee) eee eeeeee eeeee ee ee eeeee eeeee ee e eeee ee ee eeee eeeeeee (8 eeee) ee eeeeeee (8 eM) (MMMMMMM: eeeeeeeeee). M eeee ee Me(MMe)8 (8.88 eeee, 8 eee%) eee MeMeee (8.88 eeee, 8 eee%) ee eeeeeee (8 eM) eee eeeeeee eee 8 eee ee ee eee eeee eeeee. Mee eeeeeeee eeeeeee eee eeeeeeee ee eeeeeeee eeeee eeeeeeeeee eee eeeeeeee ee eee eeeeeeee eeeeee eeee eeeee. M eeeeeeeee eeeeeeee eeee ee eeeeeeeeeeeeeeeeeeeeeeeeee (888; 8 eeee) ee eeeeeee (8 eM) eee eeeee eeeeeeee eeeeee 88 eee eee e eeeeee. Mee eeeeeee eee eeeeeee ee ee eeeee e eeeeee eeeeeeeeeeee ee eeeee eee 88–88 e. M 8 M eeee ee MMMM ee MMM (8.8 eeee) eee eeeee, eeeeeeee ee MeMe (8 eeee), eee eee eeeeeeeee eeeeeeeeee eee eeeeeee eee 8 e ee ee ee eeeeee eeeeeeeeee ee eee eeeeeeee. Meeeeeeeee, eee eeeeeee eee eeeeeeeee eeee MeMMe. Mee eeeeeee eeeee eee eeeeee eeeeeeeeeeee eeee M8M eee eeeee, eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeee eee eeeeeeeee ee MM8Me8 eeee eeeeee eee (8.8–8 eeee eeeee) eee eee eeeeeeeeee eee eeeeeee eee 88–88 e. Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeeee eeeeeee eee eeeeeeeee ee eeeeee eeeeeeeeeeeeee, eeeeeeee ee eeeeeeee eeeeeeeeeee ee eeee-ee-eeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee.