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(Z)-Selective anti-Markovnikov or Markovnikov thiol–yne-click reactions of an internal alkyne by amide hydrogen bond control

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Abstract

Herein, we show exclusive control of stereo and regioselective thiol–yne click (TYC) reactions of internal alkynes via amide hydrogen bond control. By exploiting appropriate hydrogen bonding interactions like N–H⋯S, N–H⋯N and C–H⋯O, either (Z)-selective anti-Markovnikov or Markovnikov products could be obtained for an internal alkyne, exclusively.

Graphical abstract: (Z)-Selective anti-Markovnikov or Markovnikov thiol–yne-click reactions of an internal alkyne by amide hydrogen bond control

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Article information


Submitted
27 Jan 2020
Accepted
29 Jan 2020
First published
29 Jan 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

(Z)-Selective anti-Markovnikov or Markovnikov thiol–yne-click reactions of an internal alkyne by amide hydrogen bond control

M. Pramanik, K. Choudhuri, S. Chakraborty, A. Ghosh and P. Mal, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC00702A

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