Issue 47, 2017

Na2S-mediated synthesis of terminal alkynes from gem-dibromoalkenes

Abstract

The Na2S-mediated facile synthesis of terminal alkynes from gem-dibromoalkenes, at 20/40 °C under open flask conditions has been developed. Various precursors derived from heteroaromatic/aromatic/aliphatic aldehydes were found compatible. The reaction is proposed to proceed through the Fritsch–Buttenberg–Wiechell (FBW) rearrangement involving the corresponding vinyl carbene. Using mild reaction conditions with inexpensive Na2S·9H2O under air atmosphere has significant advantages over earlier routes.

Graphical abstract: Na2S-mediated synthesis of terminal alkynes from gem-dibromoalkenes

Supplementary files

Article information

Article type
Communication
Submitted
29 Sep 2017
Accepted
14 Nov 2017
First published
14 Nov 2017

Org. Biomol. Chem., 2017,15, 9979-9982

Na2S-mediated synthesis of terminal alkynes from gem-dibromoalkenes

R. M. Singh, D. Nandini, K. C. Bharadwaj, T. Gupta and R. P. Singh, Org. Biomol. Chem., 2017, 15, 9979 DOI: 10.1039/C7OB02431B

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