67399-11-5Relevant academic research and scientific papers
Straightforward chemoselective access to unsymmetrical dithioacetals through a thiosulfonate homologation-nucleophilic substitution sequence
Ielo, Laura,Pillari, Veronica,Gajic, Natalie,Holzer, Wolfgang,Pace, Vittorio
supporting information, p. 12395 - 12398 (2020/10/30)
A sequential C1-homologation-nucleophilic substitution tactic is presented for the preparation of rare unsymmetrical dithioacetals. The judicious selection of thiosulfonates as convenient sulfur electrophilic sources - upon the homologation event conducted on an intermediate a-halothioether - guarantees the release of the non-reactive sulfonate group, thus enabling the subsequent nucleophilic displacement with an external added thiol [(hetero)- aromatic and/or aliphatic]. Uniform high yields and excellent chemocontrol were deduced during the extensive scope study, thus documenting the versatility of the direct technique for the preparation of these unique and manipulable materials.
Bromomethyllithium-mediated chemoselective homologation of disulfides to dithioacetals
Pace, Vittorio,Pelosi, Azzurra,Antermite, Daniele,Rosati, Ornelio,Curini, Massimo,Holzer, Wolfgang
supporting information, p. 2639 - 2642 (2016/02/18)
An efficient, chemoselective homologation of disulfides and diselenides to the corresponding dithio- and diselenoacetals has been developed via the addition of bromomethyllithium. Chemoselectivity is fully preserved in the presence of concomitant electrophilic sites decorating the substrates. The synthetic potential of selected dithioacetals has been evaluated in Feringa-Fa?anas-Mastral-type Pd-catalyzed coupling with an organolithium and in the unusual 1,4-addition to a Weinreb amide.
An efficient synthesis of unsymmetrical dithioacetals from sulfoxides and thiols by the magnesium amide-induced pummerer-type reaction
Kobayashi, Kazuhiro,Kawakita, Masataka,Akamatsu, Hideki,Morikawa, Osamu,Konishi, Hisatoshi
, p. 2645 - 2647 (2007/10/03)
It has been found that the reactions of sulfoxides bearing hydrogen(s) at the α-position (R 1 SOCHR 2R 3: R 1 = alkyl or Ph; R 2 = H, alkyl, or Ph; R 3 = H or Me) with thiols (R 4SH: R 4 = alkyl or aryl) in the presence of the (diisopropylamino)magnesium
