Chemo- and enantioselective hetero-coupling of hydroxycarbazoles catalyzed by a chiral vanadium(v) complex

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Type
Article
Authors
Sako, Makoto cc
Higashida, Keigo
Kamble, Ganesh Tatya
Kaut, Kevin
Kumar, Ankit
Hirose, Yuka
Zhou, Da-Yang
Suzuki, Takeyuki cc
Rueping, Magnus cc
Maegawa, Tomohiro cc
Takizawa, Shinobu cc
Sasai, Hiroaki cc
KAUST Department
Chemical Science Program
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Date
2021
Embargo End Date
2022-06-23
Submitted Date
2021-05-22
Permanent link to this record
http://hdl.handle.net/10754/670186

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Abstract
The catalytic enantioselective oxidative hetero-coupling of arenols using a chiral vanadium(V) complex has been developed. The coupling of hydroxycarbazole derivatives with various arenols provided axially chiral biarenols with high chemo-, regio-, and enantioselectivities. The reaction took place under mild conditions and exhibited satisfactory functional group tolerance. Aerobic oxidative hetero-coupling with β-ketoesters also proceeded with high chemo- and stereoselectivities under slightly modified reaction conditions.
Citation
Sako, M., Higashida, K., Kamble, G. T., Kaut, K., Kumar, A., Hirose, Y., … Sasai, H. (2021). Chemo- and enantioselective hetero-coupling of hydroxycarbazoles catalyzed by a chiral vanadium(v) complex. Organic Chemistry Frontiers. doi:10.1039/d1qo00783a
Sponsors
This work was supported by JSPS KAKENHI Grant Numbers 20K15281 for Early-Career Scientists, JP17H05373 and JP18KK0154 in Promotion of Joint International Research (Fostering Joint International Research(B)), JST CREST Grant Number JPMJCR20R1, Daiichi Sankyo Foundation of Life, Hoansha Foundation, Iwatani Naoji foundation, and the NOVARTIS Foundation (Japan) for the Promotion of Science. We acknowledge the technical staff of the Comprehensive Analysis Center of ISIR, and Artificial Intelligence Research Center of ISIR, Osaka University (Japan).
Publisher
Royal Society of Chemistry (RSC)
Journal
ORGANIC CHEMISTRY FRONTIERS
DOI
10.1039/d1qo00783a
Additional Links
http://xlink.rsc.org/?DOI=D1QO00783A
Relations
Is Supplemented By:
  • [Dataset]
    Sako, Makoto, Higashida, Keigo, Kamble, Ganesh Tatya, Kaut, Kevin, Kumar, Ankit, Hirose, Yuka, Zhou, Da-Yang, Suzuki, Takeyuki, Rueping, Magnus, Maegawa, Tomohiro, Takizawa, Shinobu, & Sasai, Hiroaki. (2021). CCDC 1966275: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC24027H. DOI: 10.5517/ccdc.csd.cc24027h Handle: 10754/687066
  • [Dataset]
    Sako, Makoto, Higashida, Keigo, Kamble, Ganesh Tatya, Kaut, Kevin, Kumar, Ankit, Hirose, Yuka, Zhou, Da-Yang, Suzuki, Takeyuki, Rueping, Magnus, Maegawa, Tomohiro, Takizawa, Shinobu, & Sasai, Hiroaki. (2021). CCDC 2025416: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC25ZM0T. DOI: 10.5517/ccdc.csd.cc25zm0t Handle: 10754/687067
Collections
Articles; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)
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Except where otherwise noted, this item's license is described as Archived with thanks to ORGANIC CHEMISTRY FRONTIERS