A reaction mode of carbene-catalysed aryl aldehyde activation and induced phenol OH functionalization

Xingkuan Chen, Hongling Wang, Kazuki Doitomi, Chong Yih Ooi, Pengcheng Zheng, Wangsheng Liu, Hao Guo, Song Yang, Bao-An Song, Hajime Hirao () and Yonggui Robin Chi ()
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Xingkuan Chen: School of Physical & Mathematical Sciences, Nanyang Technological University
Hongling Wang: Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University
Kazuki Doitomi: School of Physical & Mathematical Sciences, Nanyang Technological University
Chong Yih Ooi: School of Physical & Mathematical Sciences, Nanyang Technological University
Pengcheng Zheng: Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University
Wangsheng Liu: Fudan University
Hao Guo: Fudan University
Song Yang: Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University
Bao-An Song: Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University
Hajime Hirao: School of Physical & Mathematical Sciences, Nanyang Technological University
Yonggui Robin Chi: School of Physical & Mathematical Sciences, Nanyang Technological University

Nature Communications, 2017, vol. 8, issue 1, 1-8

Abstract: 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.

Date: 2017
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DOI: 10.1038/ncomms15598

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