Please use this identifier to cite or link to this item:
https://doi.org/10.1126/sciadv.aay1537
DC Field | Value | |
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dc.title | Expedient synthesis of E-hydrazone esters and 1H-indazole scaffolds through heterogeneous single-atom platinum catalysis | |
dc.contributor.author | Liu, C. | |
dc.contributor.author | Chen, Z. | |
dc.contributor.author | Yan, H. | |
dc.contributor.author | Xi, S. | |
dc.contributor.author | Yam, K.M. | |
dc.contributor.author | Gao, J. | |
dc.contributor.author | Du, Y. | |
dc.contributor.author | Li, J. | |
dc.contributor.author | Zhao, X. | |
dc.contributor.author | Xie, K. | |
dc.contributor.author | Xu, H. | |
dc.contributor.author | Li, X. | |
dc.contributor.author | Leng, K. | |
dc.contributor.author | Pennycook, S.J. | |
dc.contributor.author | Liu, B. | |
dc.contributor.author | Zhang, C. | |
dc.contributor.author | Koh, M.J. | |
dc.contributor.author | Loh, K.P. | |
dc.date.accessioned | 2021-12-28T10:00:29Z | |
dc.date.available | 2021-12-28T10:00:29Z | |
dc.date.issued | 2019 | |
dc.identifier.citation | Liu, C., Chen, Z., Yan, H., Xi, S., Yam, K.M., Gao, J., Du, Y., Li, J., Zhao, X., Xie, K., Xu, H., Li, X., Leng, K., Pennycook, S.J., Liu, B., Zhang, C., Koh, M.J., Loh, K.P. (2019). Expedient synthesis of E-hydrazone esters and 1H-indazole scaffolds through heterogeneous single-atom platinum catalysis. Science Advances 5 (12) : eaay1537. ScholarBank@NUS Repository. https://doi.org/10.1126/sciadv.aay1537 | |
dc.identifier.issn | 23752548 | |
dc.identifier.uri | https://scholarbank.nus.edu.sg/handle/10635/212096 | |
dc.description.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 ?-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 ?-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 | |
dc.publisher | American Association for the Advancement of Science | |
dc.rights | Attribution-NonCommercial 4.0 International | |
dc.rights.uri | https://creativecommons.org/licenses/by-nc/4.0/ | |
dc.source | Scopus OA2019 | |
dc.type | Article | |
dc.contributor.department | CHEMISTRY | |
dc.contributor.department | PHYSICS | |
dc.contributor.department | MATERIALS SCIENCE AND ENGINEERING | |
dc.contributor.department | CHEMICAL & BIOMOLECULAR ENGINEERING | |
dc.description.doi | 10.1126/sciadv.aay1537 | |
dc.description.sourcetitle | Science Advances | |
dc.description.volume | 5 | |
dc.description.issue | 12 | |
dc.description.page | eaay1537 | |
Appears in Collections: | Staff Publications Elements |
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