Decarboxylative Hydroalkylation of Alkynes

Nicholas A. Till, Russell T. Smith, David W.C. MacMillan

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

The merger of open- and closed-shell elementary organometallic steps has enabled the selective intermolecular addition of nucleophilic radicals to unactivated alkynes. A range of carboxylic acids can be subjected to a CO2 extrusion, nickel capture, migratory insertion sequence with terminal and internal alkynes to generate stereodefined functionalized olefins. This platform has been further extended, via hydrogen atom transfer, to the direct vinylation of unactivated C-H bonds. Preliminary studies indicate that a Ni-alkyl migratory insertion is likely operative.

Original languageEnglish (US)
JournalJournal of the American Chemical Society
DOIs
StatePublished - May 2 2018

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Alkynes
Organometallics
Carboxylic acids
Olefins
Extrusion
Nickel
Atoms
Hydrogen
Insertional Mutagenesis
Alkenes
Carboxylic Acids

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

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Decarboxylative Hydroalkylation of Alkynes. / Till, Nicholas A.; Smith, Russell T.; MacMillan, David W.C.

In: Journal of the American Chemical Society, 02.05.2018.

Research output: Contribution to journalArticle

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