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Title: A reaction mode of carbene-catalysed aryl aldehyde activation and induced phenol OH functionalization
Authors: Chen, Xingkuan
Wang, Hongling
Doitomi, Kazuki
Ooi, Chong Yih
Zheng, Pengcheng
Liu, Wangsheng
Guo, Hao
Yang, Song
Song, Bao-An
Hirao, Hajime
Chi, Yonggui Robin
Keywords: Carbene
Issue Date: 2017
Source: Chen, X., Wang, H., Doitomi, K., Ooi, C. Y., Zheng, P., Liu, W., et al. (2017). A reaction mode of carbene-catalysed aryl aldehyde activation and induced phenol OH functionalization. Nature Communications, 8, 15598-.
Series/Report no.: Nature Communications
Abstract: The research in the field of asymmetric carbene organic catalysis has primarily focused on the activation of carbon atoms in non-aromatic scaffolds. Here we report a reaction mode of carbene catalysis that allows for aromatic aldehyde activation and remote oxygen atom functionalization. The addition of a carbene catalyst to the aldehyde moiety of 2-hydroxyl aryl aldehyde eventually enables dearomatization and remote OH activation. The catalytic process generates a type of carbene-derived intermediate with an oxygen atom as the reactive centre. Inexpensive achiral urea co-catalyst works cooperatively with the carbene catalyst, leading to consistent enhancement of the reaction enantioselectivity. Given the wide presence of aromatic moieties and heteroatoms in natural products and synthetic functional molecules, we expect our reaction mode to significantly expand the power of carbene catalysis in asymmetric chemical synthesis.
DOI: 10.1038/ncomms15598
Schools: School of Physical and Mathematical Sciences 
Rights: © 2017 The Author(s) (Nature Publishing Group). This work is licensed under a Creative Commons Attribution 4.0 International License. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in the credit line; if the material is not included under the Creative Commons license, users will need to obtain permission from the license holder to reproduce the material. To view a copy of this license, visit
Fulltext Permission: open
Fulltext Availability: With Fulltext
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