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- Title
Triflylpyridinium Enables Rapid and Scalable Controlled Reduction of Carboxylic Acids to Aldehydes using Pinacolborane.
- Authors
Chen, Du; Xu, Liangxuan; Yu, Yi; Mo, Qinliang; Qi, Xiaotian; Liu, Chao
- Abstract
Building up new and efficient methods for the controlled conversion of carboxylic acids to aldehydes is important. Herein, we report a rapid, modular and scalable method for the conversion of carboxylic acids to aldehydes using pinacolborane at ambient temperature, in which a triflylpyridinium reagent is used. The conversion of carboxylic acid to intermediate acylpyridinium by triflylpyridinium is new. A binary pyridine‐coordinated boronium complex is generated after reduction. The unprecedented reduction of the acylpyridinium by HBpin opens up a practically direct synthesis of aldehydes from carboxylic acids. Theoretical studies indicate that the reduction of acylpyridinium requires a lower activation free energy than that of the product aldehyde. The synthetic advantage of this protocol is further highlighted by the scalable synthesis of aldehyde via continuous flow process. Configuration retention for chiral acids are presented in those syntheses.
- Subjects
CARBOXYLIC acids; ALDEHYDES; ACTIVATION energy; CONTINUOUS processing
- Publication
Angewandte Chemie, 2023, Vol 135, Issue 2, p1
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202215168