In this Article we described a ruthenium-catalysed carbonyl addition method for alcohol production via simple unsubstituted hydrazone intermediates, but we inadvertently omitted the citation of two papers that had previously reported a similar carbanion reactivity1,2. In these papers, the authors illustrated a series of substituted hindered hydrazones (for example, tert-butyl-, trityl- and diphenyl-4-pyridylmethyl) for additions to carbonyl compounds; however, to yield the target alcohols under these circumstances, the lithium salts of these hydrazones had to be pre-formed, with subsequent C–C bond formation and removal of bulky substituents on azo-intermediates via radical decomposition.
References
Baldwin, J. E. et al. Azo anions in synthesis: use of trityl- and diphenyl-4-pyridylmethylhydrazones for reductive C−C bond formation. Tetrahedron 42, 4235–4246 (1986).
Baldwin, J. E., Bottaro, J. C., Kolhe, J. N. & Adlington, R. M. Azo anions in synthesis. Use of trityl- and diphenyl-4-pyridylmethyl-hydrazones for reductive C–C bond formation from aldehydes and ketones. J. Chem. Soc. Chem. Commun. 22–23 (1984).
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Wang, H., Dai, XJ. & Li, CJ. Addendum: Aldehydes as alkyl carbanion equivalents for additions to carbonyl compounds. Nature Chem 9, 723 (2017). https://doi.org/10.1038/nchem.2805
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DOI: https://doi.org/10.1038/nchem.2805
