Projects per year
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 language | English |
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Pages (from-to) | 10412-10416 |
Number of pages | 5 |
Journal | Chemical Science |
Volume | 10 |
Issue number | 44 |
Early online date | 27 Sept 2019 |
DOIs | |
Publication status | Published - 28 Nov 2019 |
Keywords
- formation of carbon-carbon bonds
- C-C bonds
- reaction manifolds
- nitrillium betaine
- nitrile imine (NI)
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Dive into the research topics of 'Metal free C-C bond formation via coupling of nitrile imines and boronic acids'. Together they form a unique fingerprint.Projects
- 1 Finished
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Industrial Case Account 2016 | Livingstone, Keith
Jamieson, C. (Principal Investigator), Tomkinson, N. (Co-investigator) & Livingstone, K. (Research Co-investigator)
EPSRC (Engineering and Physical Sciences Research Council)
1/10/16 → 26/08/20
Project: Research Studentship Case - Internally allocated