Na2S-mediated synthesis of terminal alkynes from gem-dibromoalkenes

Radhey M. Singh; Durgesh Nandini; Kishor Chandra Bharadwaj; Tanu Gupta; Raj Pal Singh

doi:10.1039/C7OB02431B

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Na₂S-mediated synthesis of terminal alkynes from gem-dibromoalkenes†

Radhey M. Singh,

*^a Durgesh Nandini,^ab Kishor Chandra Bharadwaj,

^a Tanu Gupta^a and Raj Pal Singh^b

Author affiliations

* Corresponding authors

^a Department of Chemistry, Institute of Science, Banaras Hindu University, Varanasi, India
E-mail: rmohan@bhu.ac.in

^b Centre for Fire Explosive and Environment Safety, Defence Research Development Organization, Delhi, India

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.

This article is part of the themed collection: Synthetic methodology in OBC

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Article information

DOI: https://doi.org/10.1039/C7OB02431B
Article type: Communication
Submitted: 29 Sep 2017
Accepted: 14 Nov 2017
First published: 14 Nov 2017

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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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Organic & Biomolecular Chemistry