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Issue 47, 2017
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Na2S-mediated synthesis of terminal alkynes from gem-dibromoalkenes

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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

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Publication details

The article was received on 29 Sep 2017, accepted on 14 Nov 2017 and first published on 14 Nov 2017


Article type: Communication
DOI: 10.1039/C7OB02431B
Citation: Org. Biomol. Chem., 2017,15, 9979-9982
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    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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