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.
“…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.…”
Herein, a Cu(II)-catalyzed facile construction of synthetically valuable spiro compounds from β-Naphthols under air is reported, in which N,N-dimethylaminoethanol (DMEA) serves as an efficient and unique C1 synthon. This transformation...
“…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.…”
Herein, a Cu(II)-catalyzed facile construction of synthetically valuable spiro compounds from β-Naphthols under air is reported, in which N,N-dimethylaminoethanol (DMEA) serves as an efficient and unique C1 synthon. This transformation...
“…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.…”
Section: Resultsmentioning
confidence: 70%
“…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.…”
Section: Resultsmentioning
confidence: 99%
“…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.…”
Section: Resultsmentioning
confidence: 99%
“…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.…”
An efficient strategy has been exploited for the synthesis of β-hydroxy phosphorodithioates via additive-free aerobic oxidative difunctionalization of alkenes with P4S10 and alcohols at room temperature. This transformation provides a...
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.