- Decarboxylative Ritter-Type Amination by Cooperative Iodine (I/III)─Boron Lewis Acid Catalysis
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Recent years have witnessed important progress in synthetic strategies exploiting the reactivity of carbocations via photochemical or electrochemical methods. Yet, most of the developed methods are limited in their scope to certain stabilized positions in molecules. Herein, we report a metal-free system based on the iodine (I/III) catalytic manifold, which gives access to carbenium ion intermediates also on electronically disfavored benzylic positions. The unusually high reactivity of the system stems from a complexation of iodine (III) intermediates with BF3. The synthetic utility of our decarboxylative Ritter-type amination protocol has been demonstrated by the functionalization of benzylic as well as aliphatic carboxylic acids, including late-stage modification of different pharmaceutical molecules. Notably, the amination of ketoprofen was performed on a gram scale. Detailed mechanistic investigations by kinetic analysis and control experiments suggest two mechanistic pathways.
- Narobe, Rok,Murugesan, Kathiravan,Schmid, Simon,K?nig, Burkhard
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p. 809 - 817
(2022/01/15)
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- Oxidative nucleophilic substitution: Transformation of alkylboronic derivatives
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An efficient amidation reaction is described in this paper. Potassium alkyltrifluoroborate salts can be transforming to amides from nitriles in the presence of copper acetate and boron trifluoride. An extension of this reaction allowed the formation of amines, ethers, and C-C bond.
- Cazorla, Clément,Métay, Estelle,Lemaire, Marc
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p. 8615 - 8621
(2011/11/30)
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- Ritter-type amidation of alkylboron derivatives with nitriles
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A mild and facile synthesis of amides from alkylboron compounds and nitriles promoted by copper acetate and BF3·OEt2 at room temperature is disclosed.
- Cazorla, Clément,Métay, Estelle,Andrioletti, Bruno,Lemaire, Marc
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scheme or table
p. 6855 - 6857
(2010/05/03)
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- A PHARMACEUTICAL COMPOSITION COMPRISING A SUBSTITUTED PHENYLPROPIONIC ACID AS A FREE ACID AND AS TERT-BUTYL AMINE SALT THEREOF
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A pharmaceutical composition comprising a compound of formula I wherein n is 1 or 2, R1 represents hydrogen, chloro, trifluoromethyl or trifluoromethoxy, R2 represents hydrogen or fluoro and R3 represents a C2-6alkyl group, wherein the compound of formula (I) is present in the composition as a free acid and as a tert-butyl amine salt thereof.
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Page/Page column 31
(2008/06/13)
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- Therapeutic agents
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The present invention provides a compound of formula I processes for preparing such compounds, their the utility in treating clinical conditions including lipid disorders (dyslipidemias) whether or not associated with insulin resistance, methods for their therapeutic use and pharmaceutical compositions containing them.
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- THERAPEUTIC AGENTS
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The present invention provides the S enantiomer of a compound of formula (I) wherein R1 represents chloro, trifluoromethyl or trifluoromethoxy, R2 represents H or fluoro and R3 represents a C2-4alkyl group as well as pharmaceutically acceptable salts, solvates and prodrugs thereof, to processes for preparing such compounds, to their the utility in treating clinical conditions including lipid disorders (dyslipidemias) whether or not associated with insulin resistance, to methods for their therapeutic use and to pharmaceutical compositions containing them.
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