Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Chan-Evans-Lam Amination of Boronic Acid Pinacol (BPin) Esters: Overcoming the Aryl Amine Problem.

Literature DB >> 27045570

Chan-Evans-Lam Amination of Boronic Acid Pinacol (BPin) Esters: Overcoming the Aryl Amine Problem.

Julien C Vantourout¹, Robert P Law², Albert Isidro-Llobet², Stephen J Atkinson², Allan J B Watson¹.

Abstract

The Chan-Evans-Lam reaction is a valuable C-N bond forming process. However, aryl boronic acid pinacol (BPin) ester reagents can be difficult coupling partners that often deliver low yields, in particular in reactions with aryl amines. Herein, we report effective reaction conditions for the Chan-Evans-Lam amination of aryl BPin with alkyl and aryl amines. A mixed MeCN/EtOH solvent system was found to enable effective C-N bond formation using aryl amines while EtOH is not required for the coupling of alkyl amines.

Entities: Chemical

Year: 2016 PMID： 27045570 DOI： 10.1021/acs.joc.6b00466

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

Keyword Cloud
Cited

8 in total

8. An Improved P^III/P^V═O-Catalyzed Reductive C-N Coupling of Nitroaromatics and Boronic Acids by Mechanistic Differentiation of Rate- and Product-Determining Steps.

Authors: Gen Li; Trevor V Nykaza; Julian C Cooper; Antonio Ramirez; Michael R Luzung; Alexander T Radosevich
Journal: J Am Chem Soc Date: 2020-03-25 Impact factor: 15.419

8 in total

Chan-Evans-Lam Amination of Boronic Acid Pinacol (BPin) Esters: Overcoming the Aryl Amine Problem.

1. Photoredox-catalyzed Direct Reductive Amination of Aldehydes without an External Hydrogen/Hydride Source.

2. Cu-Catalyzed Cross-Coupling of Nitroarenes with Aryl Boronic Acids to Construct Diarylamines.

3. Copper-Mediated C-N Coupling of Arylsilanes with Nitrogen Nucleophiles.

4. Correction to "Copper-Mediated C-N Coupling of Arylsilanes with Nitrogen Nucleophiles".

5. Chemoselective oxidation of aryl organoboron systems enabled by boronic acid-selective phase transfer.

6. Borylated Cymantrenes and Tromancenium Salts with Unusual Reactivity.

7. Catalytic Lewis Base Additive Enables Selective Copper-Catalyzed Borylative α-C-H Allylation of Alicyclic Amines.

8. An Improved P^III/P^V═O-Catalyzed Reductive C-N Coupling of Nitroaromatics and Boronic Acids by Mechanistic Differentiation of Rate- and Product-Determining Steps.