Enantioselective Au(I)/Au(III) Redox Catalysis Enabled by Chiral (P,N)-Ligands
| dc.contributor.author | Chintawar, Chetan C. | |
| dc.contributor.author | Bhoyare, Vivek W. | |
| dc.contributor.author | Mane, Manoj Vasisht | |
| dc.contributor.author | Patil, Nitin T. | |
| dc.date.accessioned | 2022-04-20T06:06:48Z | |
| dc.date.available | 2022-04-20T06:06:48Z | |
| dc.date.issued | 2022-04-18 | |
| dc.identifier.citation | Chintawar, C. C., Bhoyare, V. W., Mane, M. V., & Patil, N. T. (2022). Enantioselective Au(I)/Au(III) Redox Catalysis Enabled by Chiral (P,N)-Ligands. Journal of the American Chemical Society. https://doi.org/10.1021/jacs.2c02799 | |
| dc.identifier.issn | 0002-7863 | |
| dc.identifier.issn | 1520-5126 | |
| dc.identifier.doi | 10.1021/jacs.2c02799 | |
| dc.identifier.uri | http://hdl.handle.net/10754/676330 | |
| dc.description.abstract | Presented herein is the first report of enantioselective Au(I)/Au(III) redox catalysis, enabled by a newly designed hemilabile chiral (P,N)-ligand (ChetPhos). The potential of this concept has been demonstrated by the development of enantioselective 1,2-oxyarylation and 1,2-aminoarylation of alkenes which provided direct access to the medicinally relevant 3-oxy- and 3-aminochromans (up to 88% yield and 99% ee). DFT studies were carried out to unravel the enantiodetermining step, which revealed that the stronger trans influence of phosphorus allows selective positioning of the substrate in the C2-symmetric chiral environment present around nitrogen, imparting a high level of enantioselectivity | |
| dc.description.sponsorship | Generous financial support by the Science and Engineering Research Board (SERB), New Delhi (File Nos. DIA/2018/000016 and EMR/2016/007177), is gratefully acknowledged. C.C.C. and V.W.B. thank the UGC and CSIR, respectively, for the award of Senior Research Fellowships. We thank Abhik Paul from IISERB for his assistance with SC-XRD analysis. | |
| dc.publisher | American Chemical Society (ACS) | |
| dc.relation.url | https://pubs.acs.org/doi/10.1021/jacs.2c02799 | |
| dc.rights | This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of the American Chemical Society, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/doi/10.1021/jacs.2c02799. | |
| dc.title | Enantioselective Au(I)/Au(III) Redox Catalysis Enabled by Chiral (P,N)-Ligands | |
| dc.type | Article | |
| dc.contributor.department | KAUST Catalysis Centre, King Abdullah University of Science and Technology (KAUST), Thuwal 23955-6900, Saudi Arabia | |
| dc.contributor.department | KAUST Catalysis Center (KCC) | |
| dc.identifier.journal | Journal of the American Chemical Society | |
| dc.rights.embargodate | 2023-04-18 | |
| dc.eprint.version | Post-print | |
| dc.contributor.institution | Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhauri, Bhopal 462 066, India | |
| dc.contributor.institution | Physical Chemistry Division, CSIR−National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411 008, India | |
| dc.contributor.institution | Academy of Scientific and Innovative Research (AcSIR), New Delhi 110 025, India | |
| kaust.person | Mane, Manoj Vasisht |