Hydrochalcogenation of Symmetrical and Unsymmetrical Buta-1,3-diynes with Diaryl Dichalcogenides: Facile Entry to (Z)-1-(Organylchalcogeno)but-1-en-3-yne Derivatives

Cheerladinne Venkateswarlu; Srinivasan Chandrasekaran

doi:10.1055/s-0034-1379330

Synthesis, Table of Contents

Synthesis 2015; 47(03): 395-410
DOI: 10.1055/s-0034-1379330

paper

Hydrochalcogenation of Symmetrical and Unsymmetrical Buta-1,3-diynes with Diaryl Dichalcogenides: Facile Entry to (Z)-1-(Organylchalcogeno)but-1-en-3-yne Derivatives

Cheerladinne Venkateswarlu

Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, Karnataka, India, Fax: +91(80)23600529 Email: scn@orgchem.iisc.ernet.in

,

Srinivasan Chandrasekaran*

Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, Karnataka, India, Fax: +91(80)23600529 Email: scn@orgchem.iisc.ernet.in

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Abstract

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Abstract

This work describes an efficient and stereoselective method for the hydrothiolation and -selenation of buta-1,3-diyne derivatives using diaryl disulfides or diselenides, respectively. In the presence of rongalite (HOCH₂SO₂Na) and potassium carbonate, buta-1,3-diynes undergo stereoselective addition of the thiolate or selenide anion generated in situ from diaryl disulfides or diselenides to afford the corresponding (Z)-1-sulfanyl- or (Z)-1-selanylalk-1-en-3-yne derivatives, respectively. The reaction of buta-1,3-diynes with diaryl disulfides or diselenides at higher temperature (70 °C) gave a mixture of monothiolation/selenation and bisthiolation/selenation products in moderate to good yields.

Key words

hydrochalcogenation - buta-1,3-diynes - aryl dichalcogenides - rongalite - reductive cleavage

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References

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