Expedient synthesis of E-hydrazone esters and 1H-indazole scaffolds through heterogeneous single-atom platinum catalysis
Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review
Author(s)
Detail(s)
Original language | English |
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Article number | eaay1537 |
Journal / Publication | Science Advances |
Volume | 5 |
Issue number | 12 |
Online published | 6 Dec 2019 |
Publication status | Published - 6 Dec 2019 |
Externally published | Yes |
Link(s)
DOI | DOI |
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Attachment(s) | Documents
Publisher's Copyright Statement
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Link to Scopus | https://www.scopus.com/record/display.uri?eid=2-s2.0-85076535464&origin=recordpage |
Permanent Link | https://scholars.cityu.edu.hk/en/publications/publication(991481ca-f2fd-46d4-9740-245da916e6c9).html |
Abstract
Unprotected E-hydrazone esters are prized building blocks for the preparation of 1H-indazoles and countless other N-containing biologically active molecules. Despite previous advances, efficient and stereoselective synthesis of these compounds remains nontrivial. Here, we show that Pt single atoms anchored on defect-rich CeO2 nanorods (Pt1/CeO2), in conjunction with the alcoholysis of ammonia borane, promotes exceptionally E-selective hydrogenation of α-diazoesters to afford a wide assortment of N-H hydrazone esters with an overall turnover frequency of up to 566 hours−1 upon reaction completion. The α-diazoester substrates could be generated in situ from readily available carboxylic esters in one-pot hydrogenation reaction. Utility is demonstrated through concise, scalable synthesis of 1H-indazole–derived pharmaceuticals and their 15N-labeled analogs. The present protocol highlights a key mechanistic nuance wherein simultaneous coordination of a Pt site with the diazo N=N and ester carbonyl motifs plays a central role in controlling stereoselectivity, which is supported by density functional theory calculations. Copyright © 2019 The Authors, some rights reserved.
Research Area(s)
Citation Format(s)
Expedient synthesis of E-hydrazone esters and 1H-indazole scaffolds through heterogeneous single-atom platinum catalysis. / Liu, Cuibo; Chen, Zhongxin; Yan, Huan et al.
In: Science Advances, Vol. 5, No. 12, eaay1537, 06.12.2019.
In: Science Advances, Vol. 5, No. 12, eaay1537, 06.12.2019.
Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review
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