Scope of Aminomethylations via Suzuki−Miyaura Cross-Coupling of Organotrifluoroborates

2008/02/20 by Gary A. Molander, Paul E. Gormisky, Deidre L. Sandrock · 23 citations
Chemistry · #Catalytic Cross-Coupling Reactions #Catalytic C–H Functionalization Methods #Organoboron and organosilicon chemistry

paper · doi:10.1021/jo800183q

Abstract

We previously reported the Suzuki-Miyaura reaction of N,N-dialkylaminomethyltrifluoroborates with aryl bromides. Herein, we report a further investigation of the scope and limitations of this palladium-catalyzed aminomethylation reaction. Aryl chlorides, iodides, and triflates coupled in good to excellent yields to give N,N-dialkylbenzylic amines. The aminomethylation of alkenyl bromides was also examined.

Cited by

• Organotrifluoroborates: Another Branch of the Mighty Oak
• Reinvestigation of Aminomethyltrifluoroborates and Their Application in Suzuki−Miyaura Cross-Coupling Reactions
• Suzuki–Miyaura Cross-Coupling of Potassium Trifluoro(N-methylheteroaryl)borates with Aryl and Heteroaryl Halides
• Preparation of potassium alkoxymethyltrifluoroborates and their cross-coupling with aryl chlorides. [europepmc]
• Efficient cross-coupling of secondary alkyltrifluoroborates with aryl chlorides--reaction discovery using parallel microscale experimentation. [europepmc]
• Cross-coupling of cyclopropyl- and cyclobutyltrifluoroborates with aryl and heteroaryl chlorides. [europepmc]
• Multistep synthesis of complex boronic acids from simple MIDA boronates. [europepmc]
• Scope of the Suzuki-Miyaura cross-coupling reaction of potassium trifluoroboratoketohomoenolates. [europepmc]
• Suzuki-Miyaura cross-coupling reactions of primary alkyltrifluoroborates with aryl chlorides. [europepmc]
• Potassium trifluoroborate salts as convenient, stable reagents for difficult alkyl transfers. [europepmc]
• Organotrifluoroborates and monocoordinated palladium complexes as catalysts--a perfect combination for Suzuki-Miyaura coupling. [europepmc]
• Synthesis of amidomethyltrifluoroborates and their use in cross-coupling reactions. [europepmc]
• Cross-coupling of mesylated phenol derivatives with potassium ammonio- and amidomethyltrifluoroborates. [europepmc]
• Synthesis and cross-coupling of sulfonamidomethyltrifluoroborates. [europepmc]
• Reinvestigation of aminomethyltrifluoroborates and their application in Suzuki-Miyaura cross-coupling reactions. [europepmc]
• Synthesis and cross-coupling reactions of imidomethyltrifluoroborates with aryl chlorides. [europepmc]
• Iridium-Catalyzed Allylic Amination Route to α-Aminoboronates: Illustration of the Decisive Role of Boron Substituents. [europepmc]
• Iterative Cross-Couplng with MIDA Boronates: Towards a General Platform for Small Molecule Synthesis. [europepmc]
• Rapid and efficient access to secondary arylmethylamines. [europepmc]
• Suzuki-Miyaura cross-coupling of potassium trifluoro(N-methylheteroaryl)borates with aryl and heteroaryl halides. [europepmc]
• Tandem C(sp 3 )-H Arylation/Oxidation and Arylation/Allylic Substitution of Isoindolinones. [europepmc]
• cis -β-Bromostyrene derivatives from cinnamic acids via a tandem substitutive bromination-decarboxylation sequence. [europepmc]
• Aminomethylation of Aryl Halides using α-Silylamines Enabled by Ni/Photoredox Dual Catalysis. [europepmc]

Related

• Reinvestigation of Aminomethyltrifluoroborates and Their Application in Suzuki−Miyaura Cross-Coupling Reactions
• Suzuki–Miyaura (hetero-)aryl cross-coupling: recent findings and recommendations
• SuzukiMe: A Tactically Mild Methylation Reagent
• Suzuki–Miyaura Cross-Coupling of Potassium Trifluoro(N-methylheteroaryl)borates with Aryl and Heteroaryl Halides
• Sequential one-pot N -alkylation and aminocarbonylation of primary amines catalyzed by heterobimetallic Ir/Pd complexes