468060-28-8Relevant academic research and scientific papers
Copper-catalyzed hydroboration of propargyl-functionalized alkynes in water
Da Costa, Jessie S.,Braun, Roger K.,Horn, Pedro A.,Lüdtke, Diogo S.,Moro, Angélica V.
, p. 59935 - 59938 (2016)
The Cu-catalyzed hydroboration of alkynes in operationally simple and environmentally friendly conditions is reported. The reactions are performed in water, at room temperature, under micellar catalysis. Conditions to form the α or β borylated products se
Gram-Negative Antibiotic Active through Inhibition of an Essential Riboswitch
Geddes, Emily J.,Hergenrother, Paul J.,Lau, Gee W.,Lee, Hyang Yeon,Motika, Stephen E.,Ulrich, Rebecca J.
supporting information, p. 10856 - 10862 (2020/07/04)
Multidrug-resistant Gram-negative (GN) infections for which there are few available treatment options are increasingly common. The development of new antibiotics for these pathogens is challenging because of the inability of most small molecules to accumulate inside GN bacteria. Using recently developed predictive guidelines for compound accumulation in Escherichia coli, we have converted the antibiotic Ribocil C, which targets the flavin mononucleotide (FMN) riboswitch, from a compound lacking whole-cell activity against wild-type GN pathogens into a compound that accumulates to a high level in E. coli, is effective against Gram-negative clinical isolates, and has efficacy in mouse models of GN infections. This compound allows for the first assessment of the translational potential of FMN riboswitch binders against wild-type Gram-negative bacteria.
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.
supporting information, p. 2322 - 2328 (2017/07/07)
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.).
Metal free catalytic hydroboration of multiple bonds in methanol using N-heterocyclic carbenes under open atmosphere
Wen, Kun,Chen, Jinbo,Gao, Feng,Bhadury, Pinaki S.,Fan, Erkang,Sun, Zhihua
, p. 6350 - 6356 (2013/09/23)
An easy to operate method of catalytic hydroboration of unsaturated compounds has been developed with wide substrate scope. Reactions of various aldimines, ketimines, α,β-unsaturated carbonyl compounds, and alkynes were successfully executed with bis(pinacolato)diboron and N-heterocyclic carbenes in methanol without requiring a transition metal or inert atmosphere.
Highly selective methods for synthesis of internal (α-) vinylboronates through efficient NHC-Cu-catalyzed hydroboration of terminal alkynes. Utility in chemical synthesis and mechanistic basis for selectivity
Jang, Hwanjong,Zhugralin, Adil R.,Lee, Yunmi,Hoveyda, Amir H.
, p. 7859 - 7871 (2011/06/27)
Cu-catalyzed methods for site-selective hydroboration of terminal alkynes, where the internal or α-vinylboronate is generated predominantly (up to >98%) are presented. Reactions are catalyzed by 1-5 mol % of N-heterocyclic carbene (NHC) complexes of copper, easily prepared from N-aryl-substituted commercially available imidazolinium salts, and proceed in the presence of commercially available bis(pinacolato)diboron [B2(pin)2] and 1.1 equiv of MeOH at -50 to -15 °C in 3-24 h. Propargyl alcohol and amine and the derived benzyl, tert-butyl, or silyl ethers as well as various amides are particularly effective substrates; also suitable are a wide range of aryl-substituted terminal alkynes, where higher α-selectivity is achieved with substrates that bear an electron-withdrawing substituent. α-Selective Cu-catalyzed hydroborations are amenable to gram-scale procedures (1 mol % catalyst loading). Mechanistic studies are presented, indicating that α selectivity arises from the structural and electronic attributes of the NHC ligands and the alkyne substrates. Consistent with suggested hypotheses, catalytic reactions with a Cu complex, derived from an N-adamantyl-substituted imidazolinium salt, afford high β selectivity with the same class of substrates and under similar conditions.
Vicinal diboronates in high enantiomeric purity through tandem site-selective NHC-Cu-catalyzed boron-copper additions to terminal alkynes
Lee, Yunmi,Jang, Hwanjong,Hoveyda, Amir H.
scheme or table, p. 18234 - 18235 (2010/04/25)
(Chemical Equation Presented) A Cu-catalyzed protocol for conversion of terminal alkynes to enantiomerically enriched diboronates is reported. In a single vessel, a site-selective hydroboration of an alkyne leads to the corresponding terminal vinylboronat
