Copper‐Catalyzed Decarboxylative Alkylselenation of Propiolic Acids with Se Powder and Epoxides

Abstract

A copper-catalyzed decarboxylative alkylselenation of propiolic acids with Se powder and epoxides leading to alkynyl selenides is developed. This protocol not only provides an approach to obtain alkynyl selenides with the formation of double CÀ Se bonds, but also expands the applicability of alkynyl carboxylic acid.

Recent advances in catalytic decarboxylative transformations of carboxylic acid groups attached to a non-aromatic sp2or sp carbon

“…In 2021, Wu et al described a novel method to incorporate a selenium atom into an organic molecule using metallic selenium as the source. 86 The strategy offers a unique approach for obtaining highly functionalized alkynyl selenides through a copper-catalyzed three-component reaction involving an epoxide, an excess of alkynoic acid and Se powder with the formation of two C–Se bonds in a highly selective manner (Scheme 74).…”

Recent Advances in Design and Synthesis of Diselenafulvenes, Tetraselenafulvalenes, and Their Tellurium Analogs and Application for Materials Sciences

“…Phenylacetylene was deprotonated with n -BuLi in THF solution at low temperature (−78 °C) in order to obtain lithium phenylalkyneselenolate 4 . This lithium derivative was used in situ in the insertion reaction with elemental selenium producing compound 4 in 94% yield ( Scheme 2 ) [ 38 , 39 ].…”

“… The preparation of ( E )-2-benzylidene-4-phenyl-1,3-diselenole 3 from phenylacetylene and selenium [ 38 , 39 ]. …”

Copper-Mediated Decarboxylative Coupling of 3-Indoleacetic Acids with Pyrazolones

“…Gooßen and other groups reported metal-catalyzed decarboxylative arylation reactions with electron-poor benzoic acids . Alkynyl and alkenyl carboxylic acids were widely reported as alkynyl and alkenyl sources. , Li and co-workers achieved construction of C­(sp 3 )–halo, C­(sp 3 )–C, and C­(sp 3 )–N bonds with aliphatic carboxylic acids …”