Metal free C-C bond formation via coupling of nitrile imines and boronic acids

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Abstract

The challenges of developing sustainable methods of carbon-carbon bond formation remains a topic of considerable importance in synthetic chemistry. Capitalizing on the highly reactive nature of the nitrile imine 1,3-dipole, we have developed a novel metal-free coupling of this species with aryl boronic acids. Photochemical generation of a nitrile imine intermediate and trapping with a palette of boronic acids enabled rapid and facile access to a broad library of more than 25 hydrazone derivatives in up to 92 % yield, forming a carbon-carbon bond in a metal free fashion. This represents the first reported example of direct reaction between boronic acids and a 1,3-dipole.
Original languageEnglish
Pages (from-to)10412-10416
Number of pages5
JournalChemical Science
Volume10
Issue number44
Early online date27 Sep 2019
DOIs
Publication statusPublished - 28 Nov 2019

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Boronic Acids
Nitriles
Imines
Carbon
Metals
Hydrazones
Derivatives

Keywords

  • formation of carbon-carbon bonds
  • C-C bonds
  • reaction manifolds
  • nitrillium betaine
  • nitrile imine (NI)

Cite this

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title = "Metal free C-C bond formation via coupling of nitrile imines and boronic acids",
abstract = "The challenges of developing sustainable methods of carbon-carbon bond formation remains a topic of considerable importance in synthetic chemistry. Capitalizing on the highly reactive nature of the nitrile imine 1,3-dipole, we have developed a novel metal-free coupling of this species with aryl boronic acids. Photochemical generation of a nitrile imine intermediate and trapping with a palette of boronic acids enabled rapid and facile access to a broad library of more than 25 hydrazone derivatives in up to 92 {\%} yield, forming a carbon-carbon bond in a metal free fashion. This represents the first reported example of direct reaction between boronic acids and a 1,3-dipole.",
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Metal free C-C bond formation via coupling of nitrile imines and boronic acids. / Livingstone, Keith; Betrand, Sophie; Mowat, Jenna; Jamieson, Craig.

In: Chemical Science, Vol. 10, No. 44, 28.11.2019, p. 10412-10416.

Research output: Contribution to journalArticle

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KW - formation of carbon-carbon bonds

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