Copper-catalyzed regio- and enantioselective aminoboration of alkylidenecyclopropanes: the synthesis of cyclopropane-containing β-aminoalkylboranes

Jiang, Hanchun; Tang, Xiang‐Ying; Shi, Min

doi:10.1039/c6cc01631f

Cited by 51 publications

(14 citation statements)

References 55 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Other activated alkenes, including methylene cyclopropanes (Scheme 20ii) 95 and cyclopropenes (Scheme 20iii), 96 undergo similar additions and, with appropriate ligands, high enantioselectivity can be achieved. 97 Unactivated terminal alkenes are also viable substrates and, in parallel with alkene hydroboration (Scheme 6), different regiochemistry is possible depending on the catalyst and diboron reagent combination used (Scheme 20iv). 98,99 The rationale for this reversal of regioselectivity is not fully understood, but one possibility is that the bulky NHC ligated Cu complex is only tolerated at the terminal position.…”

Section: Reactions Of Copper-boryl Species With C-c Multiple Bondsmentioning

confidence: 99%

Copper-boryl mediated organic synthesis

et al. 2018

View full text Add to dashboard Cite

Organoboron compounds are valuable synthetic intermediates that find application in a diverse variety of processes including both C-X and C-C bond-forming transformations. This has been achieved by using a variety of boron derivatives. Of these, boronate esters are probably the most versatile and, reflecting this, methods for the generation of boronate esters are of considerable current interest. Given the mild reaction conditions, good functional group tolerance, and low cost of the metal catalyst, the use of copper-boryl reagents is particularly attractive. In this review, methodologies in copper-boryl chemistry are discussed and the many different transformations possible are surveyed.

show abstract

Section: Reactions Of Copper-boryl Species With C-c Multiple Bondsmentioning

confidence: 99%

Copper-boryl mediated organic synthesis

et al. 2018

View full text Add to dashboard Cite

show abstract

“…2), [37] alkylidenecyclopropanes (eq. 3 and 4), [38,39] and cyclic alkenes (eq. 5 and 6), [40,41] yielding the corresponding acyclic or cyclic β‐aminoalkylboronates efficiently.…”

Section: Methods For the Synthesis Of β‐Aminoalkylboronic Acid Derivativesmentioning

confidence: 99%

Synthesis and Applications of β‐Aminoalkylboronic Acid Derivatives

Hall

2020

Adv Synth Catal

View full text Add to dashboard Cite

α‐Aminoalkylboronic acids display a distinct role in medicinal chemistry, and their utility has been demonstrated by the successful commercialization of three drugs: bortezomib, ixazomib, and vaborbactam. Just as α‐aminoalkylboronic acids are a bioisostere of α‐amino acids, β‐aminoalkylboronates are a bona fide bioisostere of β‐amino acids, thus they also hold promising potential in drug discovery. Moreover, β‐aminoalkylboronates are versatile synthetic intermediates that are amenable to many of the established C−B bond derivatization reactions of chiral optically enriched alkylboronates, leading to the stereocontrolled preparation of valued classes of products such as β‐amino alcohols, 1,2‐diamines, and hemiboronic acid heterocycles. In addition, β‐aminoalkylboronates were shown to act as catalysts in certain organic reactions. This review presents an overview of the strengths and limitations of current preparative methods to access β‐aminoalkylboronic acid derivatives stereoselectively with various substitution patterns. Strategically, several disconnections can be exploited to establish both functional groups. Some of the key methods include the classical Matteson asymmetric homologation chemistry, transition metal‐catalyzed aminoboration of alkenes and formal hydroboration of enamine derivatives, nucleophilic additions of boryl‐substituted carbanions onto N‐functionalized imines, borylative ring openings of aziridines, and functionalization of alpha‐boryl aldehydes.

show abstract

“…[281] Beside trying to reduce the thermal conductivity of graphene materials, the researchers also make composites with polymers with low thermal conductivity properties to reduce the overall thermal conductivity of graphene lattice, which showed promising results for future wearable energy harvesting systems. [282,283] Graphene nanoribbons (GNRs) are 1D material, and they have very similar properties (energy harvesting, thermal conductivity, electrical conductivity, and so on) with CNT and graphene. The properties of GNR for energy conversions can be easily arranged by boundary effects, doping, nano-structuring, and structural defects.…”

Section: Energy Harvesting Devicesmentioning

confidence: 99%

Carbon‐Based Nanomaterials and Sensing Tools for Wearable Health Monitoring Devices

Erdem

Derin

Shirejini

et al. 2021

Adv Materials Technologies

View full text Add to dashboard Cite

In this manner, sensor technologies have garnered great attention in various fields, including biomedicine, [2][3][4][5] environmental monitoring, [6][7][8][9] smart devices, [10] wearable devices, [11] automobile manufacturing [12] since the semiconductor materials and circuits have been developed. In particular, biosensors are powerful and innovative analytical tools that incorporate biological receptors to recognize biological analytes through either physical or chemical transducers. Primarily, bio-receptors are responsible for identifying and capturing target analytes, and the transducer basically translates biological and chemical information into the detectable signals, which are eventually converted into the concentration of the analyte. [13,14] Considering gold standard methods, such as enzyme-linked immunosorbent assay (ELISA) [15] and polymerase chain reaction (PCR)-based strategies, [16] biosensors mostly hold crucial features, such as i) short assay time, [17] ii) affordable tools and reagents, [18] iii) portability, [19] and iv) facile use and minimum user interpretation. [20] Nowadays, the applications of biosensors have been leveraged by the advancements of portable and miniaturized platforms. In particular, over the past years, wearable health monitoring devices have notable impact on continuous and real-time monitoring of health parameters, thereby accelerating the deployment of biosensing strategies to daily lives. Besides, non-invasive and ease-of-collecting information supports the benefits of the wearable systems for enhancing the awareness of individuals and communities. [21][22][23] The special features of the mechanically flexible and stable wearable sensors include remarkable means, such as portability, comfortability, light-weight, non-invasive, and reliable performance. To put it simply, wearable sensors are readily attached to skin or organ surfaces through an adhesive tape [24] or microneedles, [25] and because of such easy integrations, several researchers have focused on developing wearable sensors for real-time health monitoring. A wearable sensor is basically composed of some vital elements, including a flexible base material attached to the skin or an organ, a signal transfer electrode, and a biorecognition element. Recently, researchers have concentrated on creating integrated sensors that are able to measure various parameters simultaneously, such as pressure, temperature,The healthcare system has a drastic paradigm shift from centralized care to home-based and self-monitoring strategies; aiming to reach more individuals, minimize workload in hospitals, and reduce healthcare-associated expenses. Particularly, wearable technologies are garnering considerable interest by tracking physiological parameters through motion and activities, and monitoring biochemical markers from sweat, saliva, and tears. Through their integrations with sensors, microfluidics, and wireless communication systems, they allow physicians, family members, or individuals to monitor multiple parameters withou...

show abstract

Copper-catalyzed regio- and enantioselective aminoboration of alkylidenecyclopropanes: the synthesis of cyclopropane-containing β-aminoalkylboranes

Cited by 51 publications

References 55 publications

Copper-boryl mediated organic synthesis

Copper-boryl mediated organic synthesis

Synthesis and Applications of β‐Aminoalkylboronic Acid Derivatives

Carbon‐Based Nanomaterials and Sensing Tools for Wearable Health Monitoring Devices

Contact Info

Product

Resources

About