Oxidative Dehydrogenative Coupling of Thiols with Alkanes for the Synthesis of Sulfoxides

Abstract

An oxidative dehydrogenative coupling of thiols with alkanes via direct C(sp 3 )−H bond functionalization to form a new C−S bond and S� O double bond was developed. The present reaction features the use of readily available reagents and high step-and atom-efficiency, thus providing an efficient access to sulfoxides. A possible mechanism is proposed.

Cu(ii)-catalyzed domino construction of spironaphthalenones by dearomatization of β-naphthols and using N,N-dimethylaminoethanol as a C1 synthon

“…Spirocyclic scaffolds are valuable structural motifs in pharmaceuticals, 1 functional materials, 2 and many privileged chiral ligands. 3 Transition-metal-catalyzed dearomatization of arenes has demonstrated to be efficient for accessing various challenging but appealing spirocyclic compounds; 4 however, existing limitations such as tedious preparation of specified substrates, high cost of transition-metal catalysts and sophisticated ligands, and harsh reaction conditions have somehow hindered its application.…”

Additive-free aerobic oxidative difunctionalization of alkenes with P4S10 and alcohols to access β-hydroxy phosphorodithioates

“…On the basis of the above experiments and referring to previous reports, 13,[17][18][19] a possible reaction mechanism was proposed as shown in Scheme 4. First, the reaction of P 4 S 10 with EtOH gave the O,O-diethyl S-hydrogen phosphorodithioate 5a.…”

“…Moreover, when 4 Å MS were added in this reaction, the desired product 4aa was still obtained in 80% yield (Scheme 3d). To probe the source of the hydroxyl oxygen atom, two 18 O-labeling experiments were carried out under standard conditions. No 18 O-labeled product was detected and product 4aa was obtained in 78% yield with the addition of 5 equiv.…”

“…No 18 O-labeled product was detected and product 4aa was obtained in 78% yield with the addition of 5 equiv. of H 2 18 O in air (Scheme 3e). When the model reaction was conducted in the presence of 18 O 2 , the 18 Olabeled product was obtained in 79% yield.…”

“…of H 2 18 O in air (Scheme 3e). When the model reaction was conducted in the presence of 18 O 2 , the 18 Olabeled product was obtained in 79% yield. These results indicated that the hydroxyl oxygen atom of the product originated from dioxygen in air.…”