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An overview of N-heterocyclic carbenes

Author

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  • Matthew N. Hopkinson

    (Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster, Germany)

  • Christian Richter

    (Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster, Germany)

  • Michael Schedler

    (Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster, Germany)

  • Frank Glorius

    (Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster, Germany)

Abstract

N-heterocyclic carbenes are powerful tools in organic chemistry, with many commercially important applications; this overview describes their properties and potential uses.

Suggested Citation

  • Matthew N. Hopkinson & Christian Richter & Michael Schedler & Frank Glorius, 2014. "An overview of N-heterocyclic carbenes," Nature, Nature, vol. 510(7506), pages 485-496, June.
    • Handle: RePEc:nat:nature:v:510:y:2014:i:7506:d:10.1038_nature13384
    DOI: 10.1038/nature13384
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    1. Zhen Lei & Mizuki Endo & Hitoshi Ube & Takafumi Shiraogawa & Pei Zhao & Koichi Nagata & Xiao-Li Pei & Tomoya Eguchi & Toshiaki Kamachi & Masahiro Ehara & Takeaki Ozawa & Mitsuhiko Shionoya, 2022. "N-Heterocyclic carbene-based C-centered Au(I)-Ag(I) clusters with intense phosphorescence and organelle-selective translocation in cells," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
    2. Xiaochen Wang & Rongxin Yang & Binbing Zhu & Yuxiu Liu & Hongjian Song & Jianyang Dong & Qingmin Wang, 2023. "Direct allylic acylation via cross-coupling involving cooperative N‑heterocyclic carbene, hydrogen atom transfer, and photoredox catalysis," Nature Communications, Nature, vol. 14(1), pages 1-10, December.
    3. Hai-Ying Wang & Xin-Han Wang & Bang-An Zhou & Chun-Lin Zhang & Song Ye, 2023. "Ketones from aldehydes via alkyl C(sp3)−H functionalization under photoredox cooperative NHC/palladium catalysis," Nature Communications, Nature, vol. 14(1), pages 1-11, December.
    4. Xin Li & Yi-Lin Wang & Chan Chen & Yan-Yan Ren & Ying-Feng Han, 2022. "A platform for blue-luminescent carbon-centered radicals," Nature Communications, Nature, vol. 13(1), pages 1-8, December.
    5. Lei Zhang & Zhe Chen & Zhenpeng Liu & Jun Bu & Wenxiu Ma & Chen Yan & Rui Bai & Jin Lin & Qiuyu Zhang & Junzhi Liu & Tao Wang & Jian Zhang, 2021. "Efficient electrocatalytic acetylene semihydrogenation by electron–rich metal sites in N–heterocyclic carbene metal complexes," Nature Communications, Nature, vol. 12(1), pages 1-9, December.
    6. Liang Ling & Chenyang Hu & Linhong Long & Xue Zhang & Lixing Zhao & Liu Leo Liu & Hui Chen & Meiming Luo & Xiaoming Zeng, 2023. "Chromium-catalyzed stereodivergent E- and Z-selective alkyne hydrogenation controlled by cyclic (alkyl)(amino)carbene ligands," Nature Communications, Nature, vol. 14(1), pages 1-10, December.
    7. Jiayan Li & Ziyang Dong & Yang Chen & Zhanhui Yang & Xinen Yan & Meng Wang & Chenyang Li & Changgui Zhao, 2024. "N-Heterocyclic carbene-catalyzed enantioselective synthesis of planar-chiral cyclophanes via dynamic kinetic resolution," Nature Communications, Nature, vol. 15(1), pages 1-11, December.
    8. Zi-Jing Zhang & Nicolas Jacob & Shilpa Bhatia & Philipp Boos & Xinran Chen & Joshua C. DeMuth & Antonis M. Messinis & Becky Bongsuiru Jei & João C. A. Oliveira & Aleksa Radović & Michael L. Neidig & , 2024. "Iron-catalyzed stereoselective C–H alkylation for simultaneous construction of C–N axial and C-central chirality," Nature Communications, Nature, vol. 15(1), pages 1-10, December.
    9. Aliah El Astal-Quirós & Valentina Carrarini & Francesca Zarotti & Atiq Ur Rahman & Agustí Lledós & Cristina G. Yebra & Ernesto de Jesús & Andrea Reale, 2024. "A Doublet State Palladium(I) N-Heterocyclic Carbene Complex as a Dopant and Stabilizer for Improved Photostability in Organic Solar Cells," Energies, MDPI, vol. 17(15), pages 1-19, August.
    10. Mingrui Li & Yingtao Wu & Xiao Song & Jiaqiong Sun & Zuxiao Zhang & Guangfan Zheng & Qian Zhang, 2024. "Visible light-mediated organocatalyzed 1,3-aminoacylation of cyclopropane employing N-benzoyl saccharin as bifunctional reagent," Nature Communications, Nature, vol. 15(1), pages 1-9, December.
    11. Runbo Pei & Wenju Chang & Liancheng He & Tao Wang & Yue Zhao & Yong Liang & Xinping Wang, 2024. "Main-group compounds selectively activate natural gas alkanes under room temperature and atmospheric pressure," Nature Communications, Nature, vol. 15(1), pages 1-7, December.
    12. Peng Zhou & Wenchang Li & Jianyong Lan & Tingshun Zhu, 2022. "Electroredox carbene organocatalysis with iodide as promoter," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
    13. Yuxing Cai & Yuxin Zhao & Kai Tang & Hong Zhang & Xueling Mo & Jiean Chen & Yong Huang, 2024. "Amide C–N bonds activation by A new variant of bifunctional N-heterocyclic carbene," Nature Communications, Nature, vol. 15(1), pages 1-7, December.
    14. Qingyun Wang & Shuquan Wu & Juan Zou & Xuyang Liang & Chengli Mou & Pengcheng Zheng & Yonggui Robin Chi, 2023. "NHC-catalyzed enantioselective access to β-cyano carboxylic esters via in situ substrate alternation and release," Nature Communications, Nature, vol. 14(1), pages 1-10, December.

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