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

Na₂S-mediated synthesis of terminal alkynes from gem-dibromoalkenes

Org Biomol Chem. 2017 Dec 6;15(47):9979-9982. doi: 10.1039/c7ob02431b.

Authors

Radhey M Singh¹, Durgesh Nandini, Kishor Chandra Bharadwaj, Tanu Gupta, Raj Pal Singh

Affiliation

¹ Department of Chemistry, Institute of Science, Banaras Hindu University, Varanasi, India. rmohan@bhu.ac.in.

PMID: 29167855
DOI: 10.1039/c7ob02431b

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.