Copper-catalyzed thioamination of maleimides with diethylphosphorodithioate and amines

Abstract

The first copper-catalyzed oxidative aminophosphorothiolation of maleimides with secondary alkylamines and diethylphosphorodithioate have been established. This reaction, featuring simple, efficient catalytic system and excellent functional group tolerance, provides a concise...

Copper‐Catalyzed Oxidative Carboamination of Maleimides with Amines and α‐Bromo Carboxylates

“…The use of N ‐donor ligands gave low yield of 4 a (entries 17 and 18). FeCl 3 , as a Lewis acid additive, [8] was previously used in the aminodifunctionalization of maleimide, but gave a poor result (entry 19). Furthermore, this approach could be feasibly scaled up to 10 mmol, and the corresponding product 4 a still was obtained with high efficiency, which highlighted the reliability of this approach (entry 20).…”

Transition‐Metal‐Free C(sp2)−H Phosphorothiolation/Cyclization of o‐Hydroxyarylenaminones: Access to S‐3‐Chromon Phosphorothioates

“…Indeed, in terms of multi functionalizations involving phosphorothiolation, there are only two cases of fluoroalkylphosphorothiolation of alkenes (C−C single bonds were formed) described by Zhang et al [9] . and one case of aminophosphorothiolation of alkenes (C=C double bonds were retained) described by Wu et al [10] . However, to the best of our knowledge, there exists no report on phosphorothiolation of alkenes involving cyclilation processes.…”

“…[8] Although significant progress has been established in phosphorothiolation field, there are still encounter challenges in introducing other functionalizations or involving cyclilation processes along with phosphorothiolation (Scheme 1b). Indeed, in terms of multi functionalizations involving phosphorothiolation, there are only two cases of fluoroalkylphosphorothiolation of alkenes (CÀ C single bonds were formed) described by Zhang et al [9] and one case of aminophosphorothiolation of alkenes (C=C double bonds were retained) described by Wu et al [10] However, to the best of our knowledge, there exists no report on phosphorothiolation of alkenes involving cyclilation processes.…”

Metal-free hydrophosphorodithiolation of alkynes with P4S10 and alcohols leading to vinyl phosphorodithioates

“…4 Consequently, a number of methods have been developed to construct vinyl phosphorodithioates. 5–9 The traditional method for the synthesis of vinyl phosphorodithioates involves the reactions of Grignard reagents or vinyl lithium reagents with disulfides of O , O -dialkyl phosphorodithioic acids (Scheme 1a). 5 This strategy would produce stoichiometric quantities of metal waste accompanied by the use of excessive amounts of metal reagents and suffers from poor functional group compatibility.…”