A 13-million turnover-number anionic Ir-catalyst for a selective industrial route to chiral nicotine

Congcong Yin, Ya-Fei Jiang, Fanping Huang, Cong-Qiao Xu, Yingmin Pan, Shuang Gao, Gen-Qiang Chen, Xiaobing Ding, Shao-Tao Bai (), Qiwei Lang (), Jun Li () and Xumu Zhang ()
Additional contact information
Congcong Yin: Southern University of Science and Technology
Ya-Fei Jiang: Southern University of Science and Technology
Fanping Huang: Southern University of Science and Technology
Cong-Qiao Xu: Southern University of Science and Technology
Yingmin Pan: Southern University of Science and Technology
Shuang Gao: Southern University of Science and Technology
Gen-Qiang Chen: Southern University of Science and Technology
Xiaobing Ding: Shenzhen Catalys Technology Co., Ltd
Shao-Tao Bai: Southern University of Science and Technology
Qiwei Lang: Shenzhen Catalys Technology Co., Ltd
Jun Li: Southern University of Science and Technology
Xumu Zhang: Southern University of Science and Technology

Nature Communications, 2023, vol. 14, issue 1, 1-7

Abstract: Abstract Developing catalysts with both useful enantioselectivities and million turnover numbers (TONs) for asymmetric hydrogenation of ketones is attractive for industrial production of high-value bioactive chiral entities but remains a challenging. Herein, we report an ultra-efficient anionic Ir-catalyst integrated with the concept of multidentate ligation for asymmetric hydrogenation of ketones. Biocatalysis-like efficacy of up to 99% ee (enantiomeric excess), 13,425,000 TON (turnover number) and 224 s−1 TOF (turnover frequency) were documented for benchmark acetophenone. Up to 1,000,000 TON and 99% ee were achieved for challenging pyridyl alkyl ketone where at most 10,000 TONs are previously reported. The anionic Ir-catalyst showed a novel preferred ONa/MH instead of NNa/MH bifunctional mechanism. A selective industrial route to enantiopure nicotine has been established using this anionic Ir-catalyst for the key asymmetric hydrogenation step at 500 kg batch scale, providing 40 tons scale of product.

Date: 2023
References: View complete reference list from CitEc
Citations:

Downloads: (external link)
https://www.nature.com/articles/s41467-023-39375-8 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:14:y:2023:i:1:d:10.1038_s41467-023-39375-8

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

DOI: 10.1038/s41467-023-39375-8

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 ().