Oxygen mediated oxidative couplings of flavones in alkaline water

Xin Yang, Sophie Hui Min Lim, Jiachen Lin, Jie Wu, Haidi Tang, Fengyue Zhao, Fang Liu, Chenghua Sun, Xiangcheng Shi, Yulong Kuang, Joanne Yi Hui Toy, Ke Du, Yuannian Zhang, Xiang Wang, Mingtai Sun, Zhixuan Song, Tian Wang, Ji’en Wu, K. N. Houk () and Dejian Huang ()
Additional contact information
Xin Yang: National University of Singapore
Sophie Hui Min Lim: National University of Singapore
Jiachen Lin: National University of Singapore
Jie Wu: National University of Singapore
Haidi Tang: National University of Singapore
Fengyue Zhao: Nanjing Agricultural University
Fang Liu: Nanjing Agricultural University
Chenghua Sun: Swinburne University of Technology
Xiangcheng Shi: National University of Singapore
Yulong Kuang: National University of Singapore
Joanne Yi Hui Toy: National University of Singapore
Ke Du: National University of Singapore
Yuannian Zhang: National University of Singapore
Xiang Wang: National University of Singapore
Mingtai Sun: National University of Singapore
Zhixuan Song: National University of Singapore
Tian Wang: National University of Singapore
Ji’en Wu: National University of Singapore
K. N. Houk: University of California
Dejian Huang: National University of Singapore

Nature Communications, 2022, vol. 13, issue 1, 1-13

Abstract: Abstract Catalyzed oxidative C-C bond coupling reactions play an important role in the chemical synthesis of complex natural products of medicinal importance. However, the poor functional group tolerance renders them unfit for the synthesis of naturally occurring polyphenolic flavones. We find that molecular oxygen in alkaline water acts as a hydrogen atom acceptor and oxidant in catalyst-free (without added catalyst) oxidative coupling of luteolin and other flavones. By this facile method, we achieve the synthesis of a small collection of flavone dimers and trimers including naturally occurring dicranolomin, philonotisflavone, dehydrohegoflavone, distichumtriluteolin, and cyclodistichumtriluteolin. Mechanistic studies using both experimental and computational chemistry uncover the underlying reasons for optimal pH, oxygen availability, and counter-cations that define the success of the reaction. We expect our reaction opens up a green and sustainable way to synthesize flavonoid dimers and oligomers using the readily available monomeric flavonoids isolated from biomass and exploiting their use for health care products and treatment of diseases.

Date: 2022
References: View complete reference list from CitEc
Citations:

Downloads: (external link)
https://www.nature.com/articles/s41467-022-34123-w Abstract (text/html)

Related works:
This item may be available elsewhere in EconPapers: Search for items with the same title.

Export reference: BibTeX RIS (EndNote, ProCite, RefMan) HTML/Text

Persistent link: https://EconPapers.repec.org/RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-34123-w

Ordering information: This journal article can be ordered from
https://www.nature.com/ncomms/

DOI: 10.1038/s41467-022-34123-w

Access Statistics for this article

Nature Communications is currently edited by Nathalie Le Bot, Enda Bergin and Fiona Gillespie

More articles in Nature Communications from Nature
Bibliographic data for series maintained by Sonal Shukla () and Springer Nature Abstracting and Indexing ().