Add like
Add dislike
Add to saved papers

Synergistic Dual Role of [hmim]Br-ArSO2Cl in Cascade Sulfenylation-Halogenation of Indole: Mechanistic Insight into Regioselective C-S and C-S/C-X (X= Cl & Br) Bonds Formation in One-Pot.

Bifunctionalized indoles are an important class of biologically active heterocyclic compounds and potential drug candidates. Because of the lack of efficient synthetic methods, one pot cascade synthesis of these compounds is rare and remains a challenge. To expand this field, we herein disclose a step-economic and temperature tunable strategy wherein the synergistic effect between [hmim]Br-ArSO2Cl leads exclusively to the formation of 3-arylthio indole via sulfenylation of indole at room temperature while heating the reaction mixture at 50 ºC provided an unexpected 2-halo-3-arylthio indole with construction of C-S and C-S/C-X (X= Br & Cl) bonds without addition of any external halogenating agent via cascade sulfenylation-halogenation reactions under metal-oxidant-base-free condition. Further, insight into the reaction mechanism provides an unprecedented observation wherein the synergistic interaction between [hmim]Br-ArSO2X in the presence of catalytic amount of water generates arylsulfonic anhydride(ArSO2)2O in-situ as a new sulfur source along with the formation of [hmim]PTS as probed by NMR, ESI-MS, DART-MS and HPLC studies. Notably, the mixture of bifunctionalized 2-halo(Br/Cl)-3-arylthio indole was smoothly diversified with privileged heterocycle triazole to provide 2-(1H-triazole-1-yl)-3-arylthioindole which is an analogue of the potent indole-based anticancer agent.

Full text links

We have located links that may give you full text access.
Can't access the paper?
Try logging in through your university/institutional subscription. For a smoother one-click institutional access experience, please use our mobile app.

For the best experience, use the Read mobile app

Mobile app image

Get seemless 1-tap access through your institution/university

For the best experience, use the Read mobile app

All material on this website is protected by copyright, Copyright © 1994-2024 by WebMD LLC.
This website also contains material copyrighted by 3rd parties.

By using this service, you agree to our terms of use and privacy policy.

Your Privacy Choices Toggle icon

You can now claim free CME credits for this literature searchClaim now

Get seemless 1-tap access through your institution/university

For the best experience, use the Read mobile app