Synthesis of Terminal Ethynyl Aryl Selenides and Sulfides Based on the Retro-Favorskii Reaction of Hydroxypropargyl Precursors

Eric F Lopes; Bianca T Dalberto; Gelson Perin; Diego Alves; Thiago Barcellos; Eder J Lenardão

doi:10.1002/chem.201702493

Synthesis of Terminal Ethynyl Aryl Selenides and Sulfides Based on the Retro-Favorskii Reaction of Hydroxypropargyl Precursors

Chemistry. 2017 Oct 4;23(55):13760-13765. doi: 10.1002/chem.201702493. Epub 2017 Aug 30.

Authors

Eric F Lopes¹, Bianca T Dalberto¹, Gelson Perin¹, Diego Alves¹, Thiago Barcellos², Eder J Lenardão¹

Affiliations

¹ Centro de Ciências Químicas, Farmacêuticas e de Alimentos, Universidade Federal de Pelotas-UFPel, P.O. Box 354, CEP, 96010-900, Pelotas, RS-, Brazil.
² Laboratory of Biotechnology of Natural and Synthetic Products, Universidade de Caxias do Sul-UCS, Caxias do Sul, RS, Brazil.

PMID: 28763120
DOI: 10.1002/chem.201702493

Abstract

The retro-Favorskii reaction is an excellent way to achieve terminal alkynes. Methodologies that connect the synthesis of terminal alkynes and organochalcogen motifs are important for the construction of novel compounds. Fourteen new terminal alkynes containing either C_sp -S or C_sp -Se bonds were selectively prepared through the retro-Favorskii reaction from the respective carbinol precursors. It was discovered that terminal chalcogen alkynes were stable for weeks if stored as a solution in hexanes.

Keywords: alkynes; nucleophilic addition; selenium; sulfur; synthesis design.