Visible Light-Induced Room-Temperature Heck Reaction of Functionalized Alkyl Halides with Vinyl Arenes/Heteroarenes

Daria Kurandina, Marvin Parasram, Vladimir Gevorgyan

Research output: Contribution to journalArticle

57 Citations (Scopus)

Abstract

The first visible light-induced Pd-catalyzed Heck reaction of α-heteroatom substituted alkyl iodides and -bromides with vinyl arenes/heteroarenes has been developed. This transformation efficiently proceeds at room temperature and enables synthesis of valuable functionalized allylic systems, such as allylic silanes, boronates, germanes, stannanes, pivalates, phosphonates, phthalimides, and tosylates from the corresponding α-substituted methyl iodides. Notably, synthesis of the latter substrates failed under existing thermally induced Pd-catalyzed conditions, which highlights the importance of visible light for this transformation.

Original languageEnglish (US)
Pages (from-to)14212-14216
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number45
DOIs
StatePublished - Nov 6 2017
Externally publishedYes

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Phthalimides
Silanes
Organophosphonates
Iodides
Bromides
Temperature
Substrates
stannane
methyl iodide

Keywords

  • alkyl radicals
  • allylic synthons
  • Heck reaction
  • palladium
  • photocatalysis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

Visible Light-Induced Room-Temperature Heck Reaction of Functionalized Alkyl Halides with Vinyl Arenes/Heteroarenes. / Kurandina, Daria; Parasram, Marvin; Gevorgyan, Vladimir.

In: Angewandte Chemie - International Edition, Vol. 56, No. 45, 06.11.2017, p. 14212-14216.

Research output: Contribution to journalArticle

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