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Abstract
The need for alternative, complementary approaches to enable C-C bond formation within organic chemistry is an on-going challenge in the area. Of particular relevance are transformations that proceed in the absence of transition metal reagents. In the current study, we report a comprehensive investigation of the coupling of nitrile imines and aryl boronic acids as an approach towards sustainable C-C bond formation. In situ generation of the highly reactive 1,3-dipole facilitates a Petasis-Mannich-type coupling via a nucleophilic boronate complex. The introduction of hydrazonyl chlorides as a complementary nitrile imine source to the 2,5-tetrazoles previously reported by our laboratory further broadens the scope of the approach. Additionally, we exemplify for the first time the extension of this protocol into another 1,3-dipole, through the synthesis of aryl ketone oximes from aryl boronic acids and nitrile Noxides.
Original language | English |
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Pages (from-to) | 10591-10597 |
Number of pages | 7 |
Journal | Chemistry - A European Journal |
Volume | 26 |
Issue number | 46 |
Early online date | 19 May 2020 |
DOIs | |
Publication status | Published - 17 Aug 2020 |
Keywords
- C-C coupling
- 1,3-dipole
- nitrile imines
- nitrile oxides
- reactive intermediates
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Dive into the research topics of 'Transition metal-free coupling of 1,3-dipoles and boronic acids as a sustainable approach to C-C bond formation'. 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