Rh(<scp>iii</scp>)-catalyzed C–H activation–desymmetrization of diazabicycles with arenes: facile synthesis of functionalized cyclopentenes

Zhang, Yan; Wu, Qifan; Cui, Sunliang

doi:10.1039/c3sc52524d

Cited by 84 publications

(26 citation statements)

References 82 publications

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“…The groups of Lautens and Pineschi reported asymmetric Rh I ‐catalyzed methods to access this structural motif from diazabicycles and aryl boronic acids (Scheme ). Inspired by the cyclopentenylamine syntheses of the groups of Cui and Radhakrishnan,, we envisioned a chiral Cp x Rh III ‐catalyzed directed C−H activation–addition sequence followed by β‐heteroatom elimination to forge the two stereogenic centers of the targeted chiral cyclopentenylamine products. Herein, we report an efficient catalyst system based on a chiral Cp x Rh I (cod) precatalyst in combination with bis( o ‐toluoyl) peroxide as activating oxidant for the enantioselective synthesis of cyclopentenylamines.…”

Section: Figurementioning

confidence: 99%

An Enantioselective Cp^xRh(III)‐Catalyzed C−H Functionalization/Ring‐Opening Route to Chiral Cyclopentenylamines

Wang

Cramer

2019

Angewandte Chemie

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A chiral CpxRhIII catalyst system in situ generated from a CpxRhI(cod) precatalyst and bis(o‐toluoyl) peroxide as activating oxidant was developed for a C−H activation/ring‐opening sequence between aryl ketoxime ethers and 2,3‐diazabicyclo[2.2.1]hept‐5‐enes. This transformation provides access to densely functionalized chiral cyclopentenylamines in excellent yields and enantioselectivities of up to 97:3 er. The reported method is also well suitable for asymmetric alkenyl C−H functionalizations of α,β‐unsaturated oxime ethers, furnishing skipped dienes with high levels of enantiocontrol.

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Section: Figurementioning

confidence: 99%

An Enantioselective Cp^xRh(III)‐Catalyzed C−H Functionalization/Ring‐Opening Route to Chiral Cyclopentenylamines

Wang

Cramer

2019

Angewandte Chemie

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“…These simulated results show that the metallic and dielectric losses cause the imperfect transmission and power division. Additionally, the impedance and wavevector mismatch between the spoof SPP waveguide and SIW can also reduce transmission efficiency . Owing to the small‐radius bend used in spoof SPP waveguides, the radiation loss has also influence on the transmission performance .…”

Section: The Modified Em Parameters In the Equivalent Circuit Modelingmentioning

confidence: 99%

Programmable Hybrid Circuit Based on Reconfigurable SPP and Spatial Waveguide Modes

Gao

Zhang

et al. 2019

Adv Materials Technologies

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miniaturization of devices. In 2013, Shen et al. proposed a planar SPP waveguide with ultrathin and flexible properties. [9] Subsequently, nearly perfect conversions from spatial to SPP modes are introduced to realize high-efficiency transmissions of spoof SPPs. [10] Spoof SPPs not only possess the property of natural SPPs with field enhancement but also have their advantages, including low loss, low crosstalk, easy integration, and miniaturization. The electromagnetism physical properties of the spoof SPP device can be designed by tuning geometrical parameters. Thus, a large number of passive devices based on spoof SPPs have been reported utilizing the advantage of spoof SPP waveguide, such as filters, couplers, power dividers, and antennas. [11][12][13][14][15][16][17][18][19][20][21] Additionally, the hybrid circuits based on substrate integrated waveguide (SIW) and spoof SPP waveguide have been reported because SIW has some advantages of the significant reduction in cost, loss and radiation, and easy integration. [22,23] For passive metamaterials, their functionalities are fixed after the fabrication, which severely limits the practical values. To freely control EM waves, digital coding and programmable metamaterials are adopted in microwave frequency. [24][25][26][27][28][29][30][31] Recently, the concepts of reconfigurable and programmable of spoof plasmonic metamaterials have been proposed. Based on the reconfigurable spoof SPPs, some devices with adjustable frequency and nonlinear phenomena are realized. [32][33][34][35][36][37] Further than that, three different digital-analog functionalities can be realized by coding representation in a simple programmable system, [38] and a dual-channel spoof SPP logic "AND" gate was proposed by programming controlled of multiple modes of spoof SPPs. [39] In this work, a three-port programmable hybrid circuit is proposed and investigated, which consists of two spoof SPP waveguides loaded with the varactor diodes and the SIW. By manipulating the dispersion behaviors, EM waves only can propagate with operating frequencies lower than the cutoff frequency of the SPP waveguide but higher than that of SIW. The proposed three-port waveguide can realize the functionalities of the power division and the filtering around X-band, even Ku-band, while the corresponding transmission for the power division is around −4 dB in whole operating frequency bands. Besides, a logic "OR" gate with 2-bit coding can also A programmable hybrid circuit is proposed, which is composed of two reconfigurable spoof surface plasmon polariton (SPP) waveguides loaded with varactor diodes and a substrate integrated waveguide (SIW). By manipulating their dispersion behaviors, the band-pass effect is achieved in the hybrid circuit, in which the upper and lower cutoff frequencies are determined by the SPP waveguide and SIW, respectively. When two SPP waveguides are configured to have the same cutoff frequency that is higher than the SIW's cutoff, the proposed circuit can realize a power division; when one SP...

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“…In 2014, Zhang et al [103] reported an Rh(III)-catalyzed C-H activation-desymmetrization of diazabicycles with DG-containing arenes to afford 2-arylated cyclopentenylamines, which are key intermediates in the synthesis of important APIs (active pharmaceutical ingredients). They used both 2-pyridyl and oxime groups as the DGs.…”

Section: Dmg Assisted Ar/alkyl Couplings C(sp 2 )-H Activationsmentioning

confidence: 99%

C–H Bond Activation for Arylations

2014

Catalytic Arylation Methods

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Rh(iii)-catalyzed C–H activation–desymmetrization of diazabicycles with arenes: facile synthesis of functionalized cyclopentenes

Cited by 84 publications

References 82 publications

An Enantioselective Cp^xRh(III)‐Catalyzed C−H Functionalization/Ring‐Opening Route to Chiral Cyclopentenylamines

An Enantioselective Cp^xRh(III)‐Catalyzed C−H Functionalization/Ring‐Opening Route to Chiral Cyclopentenylamines

Programmable Hybrid Circuit Based on Reconfigurable SPP and Spatial Waveguide Modes

C–H Bond Activation for Arylations

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Rh(iii)-catalyzed C–H activation–desymmetrization of diazabicycles with arenes: facile synthesis of functionalized cyclopentenes

Cited by 84 publications

References 82 publications

An Enantioselective CpxRh(III)‐Catalyzed C−H Functionalization/Ring‐Opening Route to Chiral Cyclopentenylamines

An Enantioselective CpxRh(III)‐Catalyzed C−H Functionalization/Ring‐Opening Route to Chiral Cyclopentenylamines

Programmable Hybrid Circuit Based on Reconfigurable SPP and Spatial Waveguide Modes

C–H Bond Activation for Arylations

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An Enantioselective Cp^xRh(III)‐Catalyzed C−H Functionalization/Ring‐Opening Route to Chiral Cyclopentenylamines

An Enantioselective Cp^xRh(III)‐Catalyzed C−H Functionalization/Ring‐Opening Route to Chiral Cyclopentenylamines