Metal-free carbon–carbon bond-forming reductive coupling between boronic acids and tosylhydrazones View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2009-08-16

AUTHORS

José Barluenga, María Tomás-Gamasa, Fernando Aznar, Carlos Valdés

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. More... »

PAGES

494-499

Identifiers

URI

http://scigraph.springernature.com/pub.10.1038/nchem.328

DOI

http://dx.doi.org/10.1038/nchem.328

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1029609122

PUBMED

https://www.ncbi.nlm.nih.gov/pubmed/21378917


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