18272-84-9Relevant articles and documents
Ag(I)-promoted Suzuki-Miyaura cross-couplings of n-alkylboronic acids
Zou, Gang,Reddy, Y. Krishna,Falck
, p. 7213 - 7215 (2001)
Ag(I) salts significantly enhance palladium-catalyzed Suzuki-Miyaura cross-couplings of n-alkylboronic acids with a wide variety of aryl and alkenyl halides/triflates.
Tetrabutylammonium fluoride-assisted cross-coupling reaction between organic halides and tetraorganotin reagents catalyzed by palladium
Fugami, Keigo,Ohnuma, Shin-Ya,Kameyama, Masayuki,Saotome, Takako,Kosugi, Masanori
, p. 63 - 64 (1999)
Palladium-catalyzed cross-coupling reaction between organostannanes and organic halides are much facilitated by an addition of tetrabutylammonium fluoride (TBAF). All four substituents on tin can take part in the carbon- carbon bond formation. A butyl moi
Halogen-Bridged Methylnaphthyl Palladium Dimers as Versatile Catalyst Precursors in Coupling Reactions
Doppiu, Angelino,Goo?en, Lukas J.,Hu, Zhiyong,Pirkl, Nico,Sivendran, Nardana
supporting information, p. 25151 - 25160 (2021/10/19)
Halogen-bridged methylnaphthyl (MeNAP) palladium dimers are presented as multipurpose Pd-precursors, ideally suited for catalytic method development and preparative organic synthesis. By simply mixing with phosphine or carbene ligands, they are in situ converted into well-defined monoligated complexes. Their catalytic performance was benchmarked against state-of-the-art systems in challenging Buchwald–Hartwig, Heck, Suzuki and Negishi couplings, and ketone arylations. Their use enabled record-setting activities, beyond those achievable by optimization of the ligand alone. The MeNAP catalysts permit syntheses of tetra-ortho-substituted arenes and bulky anilines in near-quantitative yields at room temperature, allow mono-arylations of small ketones, and enable so far elusive cross-couplings of secondary alkyl boronic acids with aryl chlorides.
Mild olefin formationviabio-inspired vitamin B12photocatalysis
Bam, Radha,Pollatos, Alexandros S.,Moser, Austin J.,West, Julian G.
, p. 1736 - 1744 (2021/02/22)
Dehydrohalogenation, or elimination of hydrogen-halide equivalents, remains one of the simplest methods for the installation of the biologically-important olefin functionality. However, this transformation often requires harsh, strongly-basic conditions, rare noble metals, or both, limiting its applicability in the synthesis of complex molecules. Nature has pursued a complementary approach in the novel vitamin B12-dependent photoreceptor CarH, where photolysis of a cobalt-carbon bond leads to selective olefin formation under mild, physiologically-relevant conditions. Herein we report a light-driven B12-based catalytic system that leverages this reactivity to convert alkyl electrophiles to olefins under incredibly mild conditions using only earth abundant elements. Further, this process exhibits a high level of regioselectivity, producing terminal olefins in moderate to excellent yield and exceptional selectivity. Finally, we are able to access a hitherto-unknown transformation, remote elimination, using two cobalt catalysts in tandem to produce subterminal olefins with excellent regioselectivity. Together, we show vitamin B12to be a powerful platform for developing mild olefin-forming reactions.
