Issue 20, 2020

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

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

Supplementary files

Article information

Article type
Communication
Submitted
27 Jan 2020
Accepted
29 Jan 2020
First published
29 Jan 2020

Chem. Commun., 2020,56, 2991-2994

(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, 56, 2991 DOI: 10.1039/D0CC00702A

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