Science of Synthesis

Hopkinson, M. N.; Dix, S., Science of Synthesis: Photocatalysis in Organic Synthesis, (2018) 1, 313.

Despite the great advances made in the field of dual gold/photoredox catalysis, most of the processes developed to date have involved aryl radicals generated almost exclusively from arenediazonium salts. A 2017 report by Xu and co-workers, however, has shown that dual gold/photoredox catalysis is not limited to arylation processes and can facilitate intermolecular atom transfer thiosulfonylation reactions of alkenes.[‌43‌] Irradiation of the (trifluoromethyl)sulfanyl-containing reagent S-(trifluoromethyl) benzenesulfonothioate (‌46‌, R2 = CF3) with styrenes ‌45‌ in the presence of tris(2,2′-bipyridyl)ruthenium(II) chloride {[Ru(bipy)3]Cl2} and the N-heterocyclic carbene bearing gold(I) catalyst AuCl(IPr) [IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene] affords 1,2-difunctionalized products ‌47‌ in moderate to good yields while several important functional groups, including halogens, are tolerated (‌Scheme 18‌). Products containing alternative sulfanyl groups to (trifluoromethyl)sulfanyl can be similarly engaged upon employing the corresponding reagent ‌46‌ (R2 = Bu, Ph).

‌Meeeee 88‌ Meeeeeeeeeeeeeeee ee Meeeeeee[‌88‌]

‌Meeeeeeeeee 88‌

e ee 8:8.

Mee eeeeeeeee eeeeeeee eee eeee eeeeeeeeeeeeee ee eeeeeeee eeeeeeeee eeee eeee eeeeeeee ee ‌Meeeee 8‌ eee eeeeeeee eeeeee eeeeee-eeeeeeee eeeeeeee eeeeeee eee eeeeeee eeeeeeeeeeeee eee eeee(M) (‌Meeeee 88‌). Me eeeeeeeee ee eeeeeeeeeeee eeeeeeeee eeeeeeeeeee, eeeeeeeee ee eeeeeee *[Me(eeee)8]8+ ee [MMeMeM]+ eeeeeeee e eeee(8) eeeeeee, eeeee eee eeee eeeee eeee eeeeeeeeeeeeeeeee eeeeeee ‌88‌ ee eeeeee MMeMeMMM8 eee e eeeeeeeeeeeeee eeeeeee. Meeeeeee ee eeee eeeeeee eeeeeee ee eee eeeeeee eeee eeeeeeeee e eeeeeeee eeeeeee, eeeee ee eeeeeee ee eeeeeeeeee eee eee eeeeeeeee ee eeee(M) ee eeee(MM). Meeeee-eeeeeeee eeeeeeeee ee eee eeeeeeee eeeeeeeeeeeee eeee eeeeeeeee eee eeeeeeeeee eeeee eee eeeeeeee e eeee(MMM) eeeeeee eeeeeeee ee eeeeeeeee eeeeeeeeeee ee eeee eee M(ee8)—M eeee.

‌Meeeee 88‌ Meeeeeee Meeeeeeee Meeee eee eee Meeeeeeeeeeeeeeee ee Meeeeeee[‌88‌]

Meeeeeeeeeee Meeeeeeee

8-Meee-8-(eeeeeeeeeeeeee)eeeee Meeeeeee ‌88‌; Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee e eeeeeee ‌88‌ (8.88 eeee), e eeeeeeeeeeeeeeeee eeeeeee ‌88‌ (8.88 eeee), MeMe(MMe) (88 eee%), MeMeM8 (88 eee%), [Me(eeee)8]Me8 (8.8 eee%), eee 8,8-eeeeeeeeeeeeee (8 eM) eee eeeeeee ee ee eeeee eeeeeeeeeee eeee e 888-M eeee MMM eeeee M8 eee 8 e. Mee eeeeeee eeeee eee eeee eeeeeeee eeeeeee Meeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Meeeeeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee) eeeeeeee eee eeeeeeee.

References