Copper-Catalyzed Borylation of Acyl Chlorides with an Alkoxy Diboron Reagent: A Facile Route to Acylboron Compounds
Please always quote using this URN: urn:nbn:de:bvb:20-opus-318318
- Herein, the copper-catalyzed borylation of readily available acyl chlorides with bis(pinacolato)diboron, (B\(_{2}\)pin\(_{2}\)) or bis(neopentane glycolato)diboron (B\(_{2}\)neop\(_{2}\)) is reported, which provides stable potassium acyltrifluoroborates (KATs) in good yields from the acylboronate esters. A variety of functional groups are tolerated under the mild reaction conditions (room temperature) and substrates containing different carbon-skeletons, such as aryl, heteroaryl and primary, secondary, tertiary alkyl are applicable. AcylHerein, the copper-catalyzed borylation of readily available acyl chlorides with bis(pinacolato)diboron, (B\(_{2}\)pin\(_{2}\)) or bis(neopentane glycolato)diboron (B\(_{2}\)neop\(_{2}\)) is reported, which provides stable potassium acyltrifluoroborates (KATs) in good yields from the acylboronate esters. A variety of functional groups are tolerated under the mild reaction conditions (room temperature) and substrates containing different carbon-skeletons, such as aryl, heteroaryl and primary, secondary, tertiary alkyl are applicable. Acyl N-methyliminodiacetic acid (MIDA) boronates can also been accessed by modification of the workup procedures. This process is scalable and also amenable to the late-stage conversion of carboxylic acid-containing drugs into their acylboron analogues, which have been challenging to prepare previously. A catalytic mechanism is proposed based on in situ monitoring of the reaction between p-toluoyl chloride and an NHC-copper(I) boryl complex as well as the isolation of an unusual lithium acylBpinOBpin compound as a key intermediate.…
Author: | Xiaolei Zhang, Alexandra Friedrich, Todd B. Marder |
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URN: | urn:nbn:de:bvb:20-opus-318318 |
Document Type: | Journal article |
Faculties: | Fakultät für Chemie und Pharmazie / Institut für Anorganische Chemie |
Language: | English |
Parent Title (English): | Chemistry—A European Journal |
Year of Completion: | 2022 |
Volume: | 28 |
Issue: | 42 |
Article Number: | e202201329 |
Source: | Chemistry—A European Journal 2022, 28(42):e202201329. DOI: 10.1002/chem.202201329 |
DOI: | https://doi.org/10.1002/chem.202201329 |
Dewey Decimal Classification: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 546 Anorganische Chemie |
Tag: | boronate; borylation; carbonyl; catalysis; copper |
Release Date: | 2023/07/05 |
Licence (German): | CC BY: Creative-Commons-Lizenz: Namensnennung 4.0 International |