Iridium-catalysed regioselective borylation of carboranes via direct B–H activation

Cheng, Ruofei; Qiu, Zaozao; Xie, Zuowei

doi:10.1038/ncomms14827

Cited by 136 publications

(49 citation statements)

References 71 publications

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“…[14] Substrate scope investigation showedt hat steric factors played an importantr ole in such borylation reaction. [14] Substrate scope investigation showedt hat steric factors played an importantr ole in such borylation reaction.…”

Section: Catalytic Selective Cage B(36)àh Functionalizationmentioning

confidence: 99%

Transition‐Metal‐Catalyzed Selective Cage B−H Functionalization of o‐Carboranes

Quan

Qiu

Xie

2018

Chemistry A European J

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125

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Carboranes are a class of carbon-boron molecular clusters with unusual thermal and chemical stabilities. They have been proved as very useful building blocks in supramolecular design, optoelectronics, nanomaterials, boron neutron capture therapy agents and organometallic/coordination chemistry. Thus, the functionalization of o-carboranes has received growing interests. Over the past decades, most of the works in this area have been focused on cage carbon functionalization as the weakly acidic cage C-H proton can be readily deprotonated by strong bases. In sharp contrast, selective cage B-H activation/functionalization among chemically very similar ten B-H vertices is very challenging. Considering the differences in electron density of ten cage B-H bonds in o-carborane and the nature of transition metal complexes, we have tackled this selectivity issue by means of organometallic chemistry. Our strategy is as follows: using electron-rich transition metal catalysts for the functionalization of the most electron-deficient B(3,6)-H vertices (bonded to both cage CH vertices); using electron-deficient transition-metal catalysts for the functionalization of relatively electron-rich B(8,9,10,12)-H vertices (with no bonding to both cage CH vertices); and using the combination of directing groups and electrophilic transition metal catalysts for the functionalization of B(4,5,7,11)-H vertices (bonded to only one cage CH vertex). Successful applications of such a strategy result in the preparation of a large variety of cage B-functionalized carboranes in a regioselective and catalytic manner, which are inaccessible by other means. It is believed that as this field progresses, other cage B-functionalized carboranes are expected to be synthesized, and the results detailed in this concept article will further these efforts.

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Section: Catalytic Selective Cage B(36)àh Functionalizationmentioning

confidence: 99%

Transition‐Metal‐Catalyzed Selective Cage B−H Functionalization of o‐Carboranes

Quan

Qiu

Xie

2018

Chemistry A European J

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125

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“…The MEC reactor was constructed as described by Cheng et al with some modification. 24,25 A single-chamber reactor was made from Plexiglas with 15 mL internal volume (3 cm diameter and 2 cm length). The anode and the cathode were located at each end of the cylinder with a 2 cm distance.…”

Section: Methodsmentioning

confidence: 99%

Hydrogen Production from Makgeolli Wastewater Using a Single‐Chamber Microbial Electrolysis Cell

Kim

Jeon

et al. 2019

Bulletin Korean Chem Soc

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Domestic and industrial wastewaters are subject to the biological treatment process before discharged to environment. In that process, organic substances contained in the wastewater are degraded by microorganisms. Microbial electrolysis cells (MECs) are suitable technology for wastewater treatment, simultaneously producing hydrogen. In most case, however, a significant amount of methane instead of hydrogen is produced when the wastewater is used for MECs. Here we show that hydrogen is the main product when Makgeolli wastewater (MW) is used as a substrate in a single‐chamber MEC which was operated using acetate and MW. Although current generation profiles vary according to the substrate type and the applied voltage, hydrogen portions were maintained over 90% at −0.6 V and −0.8 V with production rates of 0.95 and 1.55 m3H2/m3/d, respectively. This result shows a possibility of implementing MECs in the real wastewater treatment and hydrogen production.

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“…15 Coulombic efficiency was calculated as CE = C p /C th Á100%, where C p is the total charge calculated by integrating the current over time, and C th is the theoretical amount of charge available based on the COD removed in the MFC. 16 The pH of a liquid is a measure of its acidity or alkalinity and reflects the amount of positively charged hydrogen ions dissolved in the liquid. Many such ions make the liquid acidic.…”

Section: Experimental Conditionsmentioning

confidence: 99%

Using 3D Composite Electrode Materials for Electricity Generation from Swine Wastewater in a Dual-Chamber Microbial Fuel Cells

Lai

Lou

Lin

2017

Journal of the Chinese Chemical Society

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Swine wastewater has a high concentration of organic matter, suspended solids, and higher ammonia nitrogen, odor, complex polluting ingredients, and large emissions. A two‐chambered cubic microbial fuel cell (MFC) was used to evaluate the effect of a novel three‐dimensional (3D) electrode made of 3D iron composites and 3D stainless composites on the electricity generation. Swine wastewater with a total chemical oxygen demand (TCOD) of 3688 ± 300 mg/L was used as the feedstock in the anode chamber. The MFC reactor was incubated with an initial pH of 7.0 in an air shaker with a temperature of ~35°C and 100 rpm in the fed‐batch mode. A fixed external resistance (R) of 100 Ω was connected between the electrodes, and the closed‐circuit potentials of the MFCs were recorded every 5 min. The results showed that using an iron–carbon fiber composite 3D electrode resulted in a peak electricity generation of 321 mV on the first 2 days and maintained a stable voltage of 163 mV during the second to sixth days. The COD removal efficiency could reach 75%. Using a stainless–carbon fiber 3D electrode could generate a peak voltage of only 29.5 mV and a stable voltage of 15.2 mV with a COD removal efficiency of 54%.

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Iridium-catalysed regioselective borylation of carboranes via direct B–H activation

Cited by 136 publications

References 71 publications

Transition‐Metal‐Catalyzed Selective Cage B−H Functionalization of o‐Carboranes

Transition‐Metal‐Catalyzed Selective Cage B−H Functionalization of o‐Carboranes

Hydrogen Production from Makgeolli Wastewater Using a Single‐Chamber Microbial Electrolysis Cell

Using 3D Composite Electrode Materials for Electricity Generation from Swine Wastewater in a Dual-Chamber Microbial Fuel Cells

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