Journal
NATURE CHEMISTRY
Volume 8, Issue 4, Pages 360-367Publisher
NATURE PUBLISHING GROUP
DOI: 10.1038/NCHEM.2439
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Funding
- Pfizer
- Studienstiftung des deutschen Volkes (German National Academic Foundation)
- Alexander-von-Humboldt foundation
- Erasmus+
- Swiss National Science Foundation
- EPSRC [EP/K009494/1, EP/M004120/1]
- Engineering and Physical Sciences Research Council [EP/K009494/1] Funding Source: researchfish
- EPSRC [EP/K009494/1] Funding Source: UKRI
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The ability to form multiple carbon-carbon bonds in a controlled sequence and thus rapidly build molecular complexity in an iterative fashion is an important goal in modern chemical synthesis. In recent times, transition-metal-catalysed coupling reactions have dominated in the development of C-C bond forming processes. A desire to reduce the reliance on precious metals and a need to obtain products with very low levels of metal impurities has brought a renewed focus on metal-free coupling processes. Here, we report the in situ preparation of reactive allylic and benzylic boronic acids, obtained by reacting flow-generated diazo compounds with boronic acids, and their application in controlled iterative C-C bond forming reactions is described. Thus far we have shown the formation of up to three C-C bonds in a sequence including the final trapping of a reactive boronic acid species with an aldehyde to generate a range of new chemical structures.
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