1447974-53-9Relevant academic research and scientific papers
Combining Copper-Catalyzed Hydroboration with Palladium-Catalyzed Suzuki Coupling for the One-pot Synthesis of Arylallylamines under Micellar Conditions
Horn, Pedro A.,Braun, Roger K.,Isoppo, Victória G.,Costa, Jessie S. da,Lüdtke, Diogo S.,Moro, Angélica V.
, p. 2322 - 2328 (2017)
Herein we report the one-pot dual-metal catalytic synthesis of arylallylamines, by combination of a Cu-catalyzed hydroboration with a Pd-catalyzed Suzuki arylation, using a broad range of aryl halides. Importantly, the reaction sequence was entirely performed in water, in the presence of small amounts of SPGS-550M, without the need of solvent switch or addition of organic co-solvents, rendering it operationally simple and environmentally benign. The usefulness of this methodology was highlighted in a short synthesis of the pharmaceutically important compound naftifine. (Figure presented.).
Solvent-dependent enantiodivergence in the chlorocyclization of unsaturated carbamates
Garzan, Atefeh,Jaganathan, Arvind,Salehi Marzijarani, Nastaran,Yousefi, Roozbeh,Whitehead, Daniel C.,Jackson, James E.,Borhan, Babak
supporting information, p. 9015 - 9021 (2013/07/26)
A remarkable solvent-controlled enantiodivergence is seen in the hydroquinidine 1,4-phthalazinediyl diether ((DHQD)2PHAL)-catalyzed chlorocyclization of unsaturated carbamates. Eyring plot analyses of this previously unreported reaction are used to probe and compare the R- and S-selective pathways. In the CHCl3/hexanes solvent system, the pro-R process shows a surprising increase in selectivity with increasing temperature. These studies point to a strongly solvent-dependent entropy-enthalpy balance between the pro-R and pro-S pathways. Two solvents, two enantiomers: Enantiodivergent hydroquinidine 1,4-phthalazinediyl diether ((DHQD) 2PHAL)-catalyzed chlorocyclization of unsaturated carbamates, controlled solely by the choice of solvent, yields oxazolidinones in high enantioselectivity (see scheme; DCDMH=1,3-dichloro-5,5-dimethyl hydantoin). The origin of the observed enantiodivergence is traced back to a solvent-selected entropy-enthalpy balance between pro-R and pro-S pathways that dictates the course of the reaction. Copyright
