An unprecedented reactivity of (E)‐β‐iodovinyl sulfones in the presence of NaOAc is reported. The (E)‐β‐iodovinyl sulfones were treated with NaOAc in DMSO/H2O to yield β‐keto sulfones in moderate to high yields. A novel oxidative difunctionalization of β‐iodovinyl sulfones with thiosulfonates and NaOAc in DMF has been developed. This metal‐free oxosulfenylation is an operationally simple to access a wide range of β‐keto thiosulfones (α‐thioaryl‐β‐keto sulfones) in moderate to high yields. The transformations were reliable at gram‐scale, thus illustrating its efficiency and practicality. A plausible mechanism for the protocol is also proposed.
A new and highly efficient vicinal thiosulfonylation of 1,1-dibromo-1-alkenes with thiosulfonates in the presence of cesium carbonate has been developed. The metal-free diheterofunctionalization is an operationally simple to access a wide range of (E)-1,2-thiosulfonylethenes (a-aryl-b-thioarylvinyl sulfones) in moderate to high yields with high levels of stereoselectivities. Further, scalable reactions have been demonstrated for this transformation, thus illustrating its efficiency and practicality.
The review mainly focuses on the recent developments in preparing β-keto sulfones and their enormous synthetic applications. New prospects for the synthesis of β-keto thiosulfones have also been highlighted. Over...
The palladium‐catalyzed annulation between β‐iodovinyl sulfones and 2‐halophenols or 1‐bromo‐2‐naphthol or 2‐bromo‐3‐pyridinol is presented. The annulation process involving oxa‐Michael addition‐elimination and intramolecular Heck reaction leading to form 2,3‐disubstituted benzofurans (aryl benzofuryl sulfones) in good to high yields. The regioselective tandem construction of C−O and C−C bonds has been achieved with a variety of substitution patterns. Moreover, the tandem process is reliable at gram‐scale reactions and a plausible mechanism is also proposed.
An efficient Ni-catalyzed vicinal thiosulfonylation of 1-bromoalkynes with thiosulfonates in the presence of cesium carbonate has been described. An operationally simple and highly regioselective atom transfer radical addition (ATRA) of alkynyl bromides provided a wide range of (E)-1,2-thiosulfonylethenes (alpha-aryl-beta-thioarylvinyl sulfones) in moderate to high yields. The immense substrate scope of both alkynyl bromides and thiosulfonates were explored with a broad range of functional groups. Also, the indole derived 1,1-bromoalkenes were also successfully sightseen in 1,2-thiosulfonylation process. Moreover, the Ni-catalyzed geminal-dithiolation of alkynyl bromides with N-arylthio succinimides, thus providing 1,1-dithioalkenes in high yields. The present protocol is reliable at gram-scale, and a sequential one-pot bromination and thiosulfonylation of phenylacetylene have also been achieved in scale-up synthesis. A plausible mechanism is proposed to rationalize the experimental outcome and control experiments for the vicinal thiosulfonylation.
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