Click nucleophilic conjugate additions to activated alkynes: exploring thiol-yne, amino-yne, and hydroxyl-yne reactions from (bio)organic to polymer chemistry

Josh Worch, Connor Stubbs, Matt Price, Andrew Dove

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)
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Abstract

The 1,4-conjugate addition reaction between activated alkynes or acetylenic Michael acceptors and nucleophiles (i.e., the nucleophilic Michael reaction) is a historically useful organic transformation. Despite its general utility, the efficiency and outcomes can vary widely and are often closely dependent upon specific reaction conditions. Nevertheless, with improvements in reaction design, including catalyst development and an expansion of the substrate scope to feature more electrophilic alkynes, many examples now present with features that are congruent with Click chemistry. Although several nucleophilic species can participate in these conjugate additions, ubiquitous nucleophiles such as thiols, amines, and alcohols are commonly employed and, consequently, among the most well developed. For many years, these conjugate additions were largely relegated to organic chemistry, but in the last few decades their use has expanded into other spheres such as bioorganic chemistry and polymer chemistry. Within these fields, they have been particularly useful for bioconjugation reactions and step-growth polymerizations, respectively, due to their excellent efficiency, orthogonality, and ambient reactivity. The reaction is expected to feature in increasingly divergent application settings as it continues to emerge as a Click reaction.
Original languageEnglish
Pages (from-to)6744-6776
JournalChemical Reviews
Volume121
Issue number12
DOIs
Publication statusPublished - 25 Mar 2021

Keywords

  • Michael reaction
  • activated alkynes
  • conjugate addition reactions
  • nucleophiles
  • nucleophilic attack

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