Suzuki-Miyaura Cross-Coupling Reactions of Aryl Tellurides with Potassium Aryltrifluoroborate Salts (original) (raw)
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Organic Letters, 2011
Potassium Boc-protected aminomethyltrifluoroborate, a primary aminomethyl equivalent, was synthesized successfully through a "one-pot" process. With this trifluoroborate, Suzuki-Miyaura cross-coupling reactions were investigated with a variety of both aryl-and hetaryl chlorides in good to excellent yields. Aminomethyl moieties, especially aminomethylated arenes, might be considered privileged substructures because they appear in many bioactive natural products, 1 and they are also used as important intermediates in synthetic organic chemistry (Figure 1). 2 Aminomethylarenes are often synthesized by either reduction of aryl cyanides 3 or oximes 4 (Scheme 1, path A). However, access to primary aminomethyl aryl-and hetaryl compounds with reducible functional groups would not be compatible with this method. An alternative way to install the aminomethylarene moiety is the Staudinger reaction 5 of organic azides with trivalent phosphorus compounds (Scheme 1, path B). Unfortunately, some aryl-and hetaryl azides exhibit significant thermal-or shock-sensitivity. 6 Moreover, the benzylic or pseudobenzylic halide precursors required to prepare the azides are often not readily available.
The Journal of Organic Chemistry, 2012
The introduction of an alkoxyethyl moiety onto aromatic substructures has remained a longstanding challenge for synthetic organic chemists. The main reasons are the inherent instability of alkoxyethylmetallic species and the lack of general procedures to access them. A new method utilizing a cross-coupling strategy based on the exceptional properties of organotrifluoroborates has been developed, and the method allows an easy and efficient installation of this unit on a broad range of aryl and heteroaryl bromides.
Journal of the Brazilian Chemical Society, 2009
Apresentamos aqui resultados das reações de acoplamento de diteluretos de diarila com sais de ariltrifluoroborato de potássio, usando quantidades catalíticas de Cu(OAc) 2 e bipiridina, em uma mistura de DMSO/H 2 O, sob ar atmosférico. Estas reações de acoplamento são gerais e são realizadas com diteluretos de diarila e sais de ariltrifluoroborato de potássio contendo substituintes neutros, retiradores e doadores de elétrons, fornecendo os correspondentes teluretos de diarila não simétricos em rendimentos de bons a excelentes.
Chemical Communications, 2007
General Methods. Difluoroenol silyl ethers 1 2a-2e and monofluoro silyl enol ether 2 4 were prepared as described previously. Tri-n-butyltin fluoride and a 1M toluene solution of P(t-Bu)3, were purchased from Aldrich Chemical Co. and used as received. Toluene was distilled under nitrogen over sodium prior to use. All other chemicals were used as received from commercial sources. 1 H NMR spectra were obtained on a 300-or 500-MHz spectrometer, and chemical shifts were recorded relative to a residual protonated solvent. 13 C NMR spectra were obtained at 75.5 MHz on a 300-MHz instrument, and chemical shifts were recorded relative to the solvent resonance. Both 1 H NMR and 13 C NMR chemical shifts are reported in parts per million relative to tetramethylsilane. 19 F NMR chemical shifts are reported in parts per million from CFCl 3. The solvent was CDCl 3 unless otherwise stated. The purity of products was determined by CH&N elemental analyses. Column chromatography was carried out using ACROS silicagel (0.060-0.200 mm). Thin layer chromatography (TLC) was carried out on commercially available pre-coated plates (Whatman UV 254 silica).