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Conversion of α-Haloaldehydes into Acylating Agents by an Internal Redox Reaction Catalyzed by Nucleophilic Carbenes
Abstract
Reactivity umpolung allows us to consider nontraditional bond disconnections. We report herein that treatment of an alpha-haloaldehyde with a nucleophile in the presence of catalytic amounts of nucleophilic carbenes results in an internal redox reaction giving rise to a dehalogenated acylating agent as an intermediate by a new reaction manifold. A brief illustration of the scope of this reaction is presented along with evidence supporting the direct intervention of the carbene in the acylation step.
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Cited by
Organocatalytic Ring-Opening Polymerization
Kamber, N. E., Jeong, W., Waymouth, R. M., Pratt, R. C., Lohmeijer, B. G. G., & Hedrick, J. L. (2007) · Chemical Reviews · doi:10.1021/cr068415b · Cited by 1,489
Stereoselective Synthesis of (E)-α,β-Unsaturated Esters via Carbene-Catalyzed Redox Esterification
Zeitler, K. (2006) · Organic Letters · doi:10.1021/ol052826h · Cited by 288
Shee, S., Mukherjee, S., Gonnade, R. G., & Biju, A. T. (2020) · Organic Letters · doi:10.1021/acs.orglett.0c01756 · Cited by 34
Metadata
- Authors
- Reynolds, N. T., Read de Alaniz, J., & Rovis, T.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2004-07-09
- Volume
- 126
- Issue
- 31
- Pages
- 9518-9519
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2041800381
- Cited by
- 383
- References
- 0
- FWCI
- 10.80
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: Conversion of α-Haloaldehydes into Acylating Agents by an Internal Redox Reaction Catalyzed by Nucleophilic Carbenes. https://app.cochat.ai/papers/10.1021/ja046991o
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- Reynolds, N. T., Read de Alaniz, J., & Rovis, T. (2004). Conversion of α-Haloaldehydes into Acylating Agents by an Internal Redox Reaction Catalyzed by Nucleophilic Carbenes. Journal of the American Chemical Society. https://doi.org/10.1021/ja046991o
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
