Reinvestigation of Aminomethyltrifluoroborates and Their Application in Suzuki−Miyaura Cross-Coupling Reactions

2011/03/15 by Jessica Raushel, Deidre L. Sandrock, Kanth V. Josyula +3 · 9 citations
Chemistry · #Catalytic Cross-Coupling Reactions #Chemical synthesis and alkaloids #Organophosphorus compounds synthesis

paper · doi:10.1021/jo2001066

Abstract

A reinvestigation into the chemical composition of potassium aminomethyltrifluoroborates is reported. These trifluoroborato salts have been reassigned as zwitterionic ammoniomethyltrifluoroborates. Minor adjustments to the previously disclosed reaction conditions are reported that permit a similar level of activity as nucleophiles in Suzuki-Miyaura cross-coupling reactions.

Citations

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

Cited by

• Organotrifluoroborates: Another Branch of the Mighty Oak
• Suzuki–Miyaura Cross-Coupling of Potassium Trifluoro(N-methylheteroaryl)borates with Aryl and Heteroaryl Halides
• Cross-coupling of mesylated phenol derivatives with potassium ammonio- and amidomethyltrifluoroborates. [europepmc]
• Cross-coupling of mesylated phenol derivatives with potassium alkoxymethyltrifluoroborates. [europepmc]
• Synthesis and cross-coupling reactions of imidomethyltrifluoroborates with aryl chlorides. [europepmc]
• Rapid and efficient access to secondary arylmethylamines. [europepmc]
• Nickel-catalyzed borylation of halides and pseudohalides with tetrahydroxydiboron [B2(OH)4]. [europepmc]
• Suzuki-Miyaura cross-coupling of potassium trifluoro(N-methylheteroaryl)borates with aryl and heteroaryl halides. [europepmc]
• Aminomethylation of Aryl Halides using α-Silylamines Enabled by Ni/Photoredox Dual Catalysis. [europepmc]

Related

• Suzuki–Miyaura Cross-Coupling of Potassium Trifluoro(N-methylheteroaryl)borates with Aryl and Heteroaryl Halides
• Scope of Aminomethylations via Suzuki−Miyaura Cross-Coupling of Organotrifluoroborates
• Organotrifluoroborates: Another Branch of the Mighty Oak
• Suzuki–Miyaura (hetero-)aryl cross-coupling: recent findings and recommendations
• Direct Suzuki–Miyaura cross-coupling of C(sp 2 )–B(dan) bonds: designed in pursuit of usability