Chelation-assisted Rh(iii)-catalyzed C2-selective oxidative C–H/C–H cross-coupling of indoles/pyrroles with heteroarenes

Qin, Xurong; Liu, Hu; Qin, Dekun; Wu, Qian; You, Jingsong; Zhao, Dongbing; Guo, Qiang; Huang, Xiaolei; Lan, Jingbo

doi:10.1039/c3sc22241a

Cited by 136 publications

(49 citation statements)

References 64 publications

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“…In the last few years some interesting reports on rhodium‐catalyzed dehydrogenative arene coupling reactions have appeared, often within the context of directed C−H activation. You, Lan, and co‐workers reported the chelation‐assisted rhodium(III)‐catalyzed oxidative C−H/C−H cross‐coupling of indoles and pyrroles with heteroarenes preferentially at the C2‐position (Figure ) . Their strategy allows the selective coupling between an electron‐rich heteroarene with a directing group and both electron‐rich and electron‐deficient heteroarenes.…”

Section: Intermolecular Oxidative Aromatic Couplingmentioning

confidence: 99%

“…You, Lan, and co-workers reported the chelationassisted rhodium(III)-catalyzed oxidative C À H/C À Hc rosscoupling of indoles and pyrroles with heteroarenes preferentially at the C2-position (Figure 7). [107] Their strategy allows the selective coupling between an electron-rich heteroarene with ad irecting group and both electron-rich and electrondeficient heteroarenes.F or example,2 -pyrimidyl-protected indoles or 2-methylpyrrole react with electron-poor heterocycles in the presence of a[ Cp*RhCl 2 ] 2 /AgSbF 6 catalyst system to afford coupling products 115-120.C losely related reactions were published by Kambe and co-workers at almost the same time. [108] More recently,t he procedure has been extended to the synthesis of mono-and bisarylated phenols.…”

Section: Rhodiummentioning

confidence: 99%

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Synthetic Applications of Oxidative Aromatic Coupling—From Biphenols to Nanographenes

et al. 2019

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Oxidative aromatic coupling occupies a fundamental place in the modern chemistry of aromatic compounds. It is a method of choice for the assembly of large and bewildering architectures. Considerable effort was also devoted to applications of the Scholl reaction for the synthesis of chiral biphenols and natural products. The ability to form biaryl linkages without any prefunctionalization provides an efficient pathway to many complex structures. Although the chemistry of this process is only now becoming fully understood, this reaction continues to both fascinate and challenge researchers. This is especially true for heterocoupling, that is, oxidative aromatic coupling with the chemoselective formation of a C−C bond between two different arenes. Analysis of the progress achieved in this field since 2013 reveals that many groups have contributed by pushing the boundary of structural possibilities, expanding into surface‐assisted (cyclo)dehydrogenation, and developing new reagents.

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Section: Intermolecular Oxidative Aromatic Couplingmentioning

confidence: 99%

Section: Rhodiummentioning

confidence: 99%

Synthetic Applications of Oxidative Aromatic Coupling—From Biphenols to Nanographenes

et al. 2019

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“…To address the dynamic problem, several methods have been designed . Data augmentation is a common method used in many algorithms, such as dynamic principal component analysis (DPCA) and dynamic partial least squares (DPLS).…”

Section: Introductionmentioning

confidence: 99%

Deep neural network based recursive feature learning for nonlinear dynamic process monitoring

et al. 2019

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The data collected from modern industrial processes always have nonlinear and dynamic characteristics. The recently developed deep neural network method, stacked denoising auto‐encoder (SDAE), can extract robust nonlinear latent variables from data against noise. However, it leaves the dynamic relationship unconsidered. To solve this problem, a novel algorithm named the recursive stacked denoising auto‐encoder (RSDAE) is proposed. To learn the dynamic relationship, the RSDAE focuses on the predictability of the latent variables in the recurrence to contain the most dynamic variations. After the dynamic variations are extracted by the RSDAE, there is little autocorrelation left in the residuals. Then, the residuals can be monitored by principal component analysis (PCA). For the purpose of process monitoring, corresponding fault detection statistics are developed based on the RSDAE. Finally, a numerical case and the Tennessee Eastman process benchmark are used to demonstrate the effectiveness of the proposed algorithm.

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“…The low KIE value implies that the C−H bond cleavage of arenes is not involved in the rate‐determining step ,. The above observations suggest that the reaction mechanism is distinct from those of the well‐described C−H/C−H cross‐coupling reactions between two (hetero)arenes, in which significant isotope effects are generally observed ,,,…”

Section: Methodsmentioning

confidence: 93%

Cobalt‐Catalyzed Oxidative C−H/C−H Cross‐Coupling between Two Heteroarenes

Tan

Huang

et al. 2016

Angewandte Chemie

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The first example of cobalt-catalyzed oxidative CÀH/CÀHc ross-coupling between two heteroarenes is reported, which exhibits ab road substrate scope and ah igh tolerance level for sensitive functional groups.W hen the amount of Co(OAc) 2 ·4 H 2 Oi sr educed from 6.0 to 0.5 mol %, an excellent yield is still obtained at an elevated temperature with ap rolonged reaction time.T he method can be extended to the reaction between an arene and aheteroarene. It is worth noting that the Ag 2 CO 3 oxidant is renewable. Preliminary mechanistic studies by radical trapping experiments,h ydrogen/deuterium exchange experiments,k inetic isotope effect, electron paramagnetic resonance (EPR), and high resolution mass spectrometry (HRMS) suggest that as ingle electron transfer (SET) pathwayi so perative,w hich is distinctly different from the dual CÀHb ond activation pathway that the well-described oxidative CÀH/CÀHc rosscoupling reactions between two heteroarenes typically undergo.

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Chelation-assisted Rh(iii)-catalyzed C2-selective oxidative C–H/C–H cross-coupling of indoles/pyrroles with heteroarenes

Cited by 136 publications

References 64 publications

Synthetic Applications of Oxidative Aromatic Coupling—From Biphenols to Nanographenes

Synthetic Applications of Oxidative Aromatic Coupling—From Biphenols to Nanographenes

Deep neural network based recursive feature learning for nonlinear dynamic process monitoring

Cobalt‐Catalyzed Oxidative C−H/C−H Cross‐Coupling between Two Heteroarenes

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