A multitasking functional group leads to structural diversity using designer C–H activation reaction cascades

Chen, Ying; Wang, Dongqi; Duan, Pingping; Ben, Rong; Dai, Lu; Shao, Xiaoru; Hong, Mei; Zhao, Junping; Huang, Yong

doi:10.1038/ncomms5610

Cited by 77 publications

(25 citation statements)

References 30 publications

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“…Wafer-scale heterojunction p-n diodes were fabricated using solution-processed, p-type s-SWCNTs 18 and n-type a-IGZO thin films [19][20][21] via standard photolithographic and etching techniques ( Fig. 1a; see Methods and Supporting information Sections S1 and S2 for more details).…”

Section: Toc Figurementioning

confidence: 99%

Large-Area, Low-Voltage, Antiambipolar Heterojunctions from Solution-Processed Semiconductors

et al. 2014

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The emergence of semiconducting materials with inert or dangling bond-free surfaces has created opportunities to form van der Waals heterostructures without the constraints of traditional epitaxial growth. For example, layered two-dimensional (2D) semiconductors have been incorporated into heterostructure devices with gate-tunable electronic and optical functionalities. However, 2D materials present processing challenges that have prevented these heterostructures from being produced with sufficient scalability and/or homogeneity to enable their incorporation into large-area integrated circuits. Here, we extend the concept of van der Waals heterojunctions to semiconducting p-type single-walled carbon nanotube (s-SWCNT) and n-type amorphous indium gallium zinc oxide (a-IGZO) thin films that can be solution-processed or sputtered with high spatial uniformity at the wafer scale. The resulting large-area, low-voltage p-n heterojunctions exhibit antiambipolar transfer characteristics with high on/off ratios that are well-suited for electronic, optoelectronic, and telecommunication technologies.

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Section: Toc Figurementioning

confidence: 99%

Large-Area, Low-Voltage, Antiambipolar Heterojunctions from Solution-Processed Semiconductors

et al. 2014

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“…In these cases, much success has been achieved by employing primary alcohols, aldehydes and aldoximes as precursors for the formation of C-N bonds1101112. In contrast, the ammoxidation of more easily available hydrocarbon is challenging, because of the high stability of sp 3 -hybridized C-H bonds14151617181920. In the past few years, homogeneous copper and palladium catalysts have been regarded to be active for C-N formation from C-H bonds to form amides and carbazoles as major products21222324, although these homogeneous catalysts are difficult to separate and regenerate from the reaction system.…”

mentioning

confidence: 99%

Controllable cyanation of carbon-hydrogen bonds by zeolite crystals over manganese oxide catalyst

Wang

Zhang

et al. 2017

Nat Commun

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The synthesis of organic nitriles without using toxic cyanides is in great demand but challenging to make. Here we report an environmentally benign and cost-efficient synthesis of nitriles from the direct oxidative cyanation of primary carbon-hydrogen bonds with easily available molecular oxygen and urea. The key to this success is to design and synthesize manganese oxide catalysts fixed inside zeolite crystals, forming a manganese oxide catalyst with zeolite sheath (MnOx@S-1), which exhibits high selectivity for producing nitriles by efficiently facilitating the oxidative cyanation reaction and hindering the side hydration reaction. The work delineates a sustainable strategy for synthesizing nitriles while avoiding conventional toxic cyanide, which might open a new avenue for selective transformation of carbon-hydrogen bonds.

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“…In 2014, Zhao and Huang reported a cascade reaction of N ‐phenoxyacetamides and two alkynes (Scheme ) . The original DG is auto‐cleavable but reincorporated into the product to form an enamine DG, which served as an DG auto for further direct C–H activation and alkyne annulation on the benzene ring of the previous arylalkyne substrate.…”

Section: Automatic Directing Groupsmentioning

confidence: 99%

C–H Activation and Alkyne Annulation via Automatic or Intrinsic Directing Groups: Towards High Step Economy

Zheng

Hua

2017

The Chemical Record

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Direct transformation of carbon-hydrogen bond (C-H) has emerged to be a trend for construction of molecules from building blocks with no or less prefunctionalization, leading high atom and step economy. Directing group (DG) strategy is widely used to achieve higher reactivity and selectivity, but additional steps are usually needed for installation and/or cleavage of DGs, limiting step economy of the overall transformation. To meet this challenge, we proposed a concept of automatic DG (DG ), which is auto-installed and/or auto-cleavable. Multifunctional oxime and hydrazone DG were designed for C-H activation and alkyne annulation to furnish diverse nitrogen-containing heterocycles. Imidazole was employed as an intrinsic DG (DG ) to synthesize ring-fused and π-extended functional molecules. The alkyne group in the substrates can also be served as DG for ortho-C-H activation to afford carbocycles. In this account, we intend to give a review of our progress in this area and brief introduction of other related advances on C-H functionalization using DG or DG strategies.

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A multitasking functional group leads to structural diversity using designer C–H activation reaction cascades

Cited by 77 publications

References 30 publications

Large-Area, Low-Voltage, Antiambipolar Heterojunctions from Solution-Processed Semiconductors

Large-Area, Low-Voltage, Antiambipolar Heterojunctions from Solution-Processed Semiconductors

Controllable cyanation of carbon-hydrogen bonds by zeolite crystals over manganese oxide catalyst

C–H Activation and Alkyne Annulation via Automatic or Intrinsic Directing Groups: Towards High Step Economy

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