Author: ["José Barluenga","María Tomás-Gamasa","Fernando Aznar","Carlos Valdés"]
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Abstract
The formation of carbon–carbon bonds is a fundamental transformation in organic synthesis. In spite of the myriad methods available, advantageous methodologies in terms of selectivity, availability of starting materials, operational simplicity, functional-group tolerance, environmental sustainability and economy are in constant demand. In this context, the development of new cross-coupling reactions that use catalysts based on inexpensive and non-toxic metals is attracting increasing attention. Similarly, efficient processes that do not require a metal catalyst are of extraordinary interest. Here, we report a new and efficient metal-free carbon–carbon bond-forming coupling between tosylhydrazones and boronic acids. This reaction is very general and functional-group tolerant. As the required tosylhydrazones are easily generated from carbonyl compounds, it can be seen as a reductive coupling of carbonyls, a process of high synthetic relevance that requires several steps using other methodologies. New economic and environmentally benign methods for achieving carbon–carbon bond formation are in constant demand. Here, a remarkably efficient and functional-group-tolerant, metal-free reductive cross-coupling of carbonyl compounds with boronic acids is described.Cite this article
Barluenga, J., Tomás-Gamasa, M., Aznar, F. et al. Metal-free carbon–carbon bond-forming reductive coupling between boronic acids and tosylhydrazones. Nature Chem 1, 494–499 (2009). https://doi.org/10.1038/nchem.328 