87028-10-2Relevant articles and documents
Cross-Electrophile Coupling of Vinyl Halides with Alkyl Halides
Johnson, Keywan A.,Biswas, Soumik,Weix, Daniel J.
supporting information, p. 7399 - 7402 (2016/05/24)
An improved method for the reductive coupling of aryl and vinyl bromides with alkyl halides that gave high yields for a variety of substrates at room temperature with a low (2.5 to 0.5 mol %) catalyst loading is presented. Under the optimized conditions, difficult substrates, such as unhindered alkenyl bromides, can be coupled to give the desired olefins with minimal diene formation and good stereoretention. These improved conditions also worked well for aryl bromides. For example, a gram-scale reaction was demonstrated with 0.5 mol % catalyst loading, whereas reactions at 10 mol % catalyst loading completed in as little as 20 minutes. Finally, a low-cost single-component pre-catalyst, (bpy)NiI2 (bpy=2,2′-bipyridine) that is both air- and moisture-stable over a period of months was introduced.
TPGS-750-M: A second-generation amphiphile for metal-catalyzed cross-couplings in water at room temperature
Lipshutz, Bruce H.,Ghorai, Subir,Abela, Alexander R.,Moser, Ralph,Nishikata, Takashi,Duplais, Christophe,Krasovskiy, Arkady,Gaston, Ricky D.,Gadwood, Robert C.
experimental part, p. 4379 - 4391 (2011/07/06)
An environmentally benign surfactant (TPGS-750-M), a diester composed of racemic α-tocopherol, MPEG-750, and succinic acid, has been designed and readily prepared as an effective nanomicelle-forming species for general use in metal-catalyzed cross-coupling reactions in water. Several "name" reactions, including Heck, Suzuki-Miyaura, Sonogashira, and Negishi-like couplings, have been studied using this technology, as have aminations, C-H activations, and olefin metathesis reactions. Physical data in the form of DLS and cryo-TEM measurements suggest that particle size and shape are key elements in achieving high levels of conversion and, hence, good isolated yields of products. This new amphiphile will soon be commercially available.
Ligand effects on Negishi couplings of alkenyl halides
Krasovskiy, Arkady,Lipshutz, Bruce H.
supporting information; experimental part, p. 3818 - 3821 (2011/10/01)
Negishi couplings at olefinic centers do not always occur with the anticipated maintenance of stereochemistry. The source of erosion has been traced to the ligand, and a modified method has been developed that solves the stereochemical issue and significantly improves yields of Negishi couplings in general.
Stereoselective Negishi-like couplings between alkenyl and alkyl halides in water at room temperature
Krasovskiy, Arkady,Duplais, Christophe,Lipshutz, Bruce H.
supporting information; experimental part, p. 4742 - 4744 (2010/12/25)
Mix in water and then stir. That is all that is required in this new approach to stereoselective sp3-sp2 cross-couplings between an alkyl and alkenyl halide. Prior formation of organozinc reagents is not required.
