Access to C-Stereogenic PN(sp²)P Pincer Ligands via Phosphapalladacycle Catalyzed Asymmetric Hydrophosphination
A series of PN(sp2)P ligands containing two stereogenic carbon centers were generated via the palladium(II) catalyzed asymmetric hydrophosphination of 2,6-pyridyl dienones using diphenylphosphine. Although the targeted tridentate products are powerful metal ion sequesters, poisoning of the metal cat...
| Autori principali: | , , , , |
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| Altri autori: | |
| Natura: | Journal Article |
| Lingua: | English |
| Pubblicazione: |
2022
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| Accesso online: | https://hdl.handle.net/10356/160148 |
| _version_ | 1826120062767988736 |
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| author | Foo, Ce Qing Sadeer, Abdul Li, Yongxin Pullarkat, Sumod A. Leung, Pak-Hing |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Foo, Ce Qing Sadeer, Abdul Li, Yongxin Pullarkat, Sumod A. Leung, Pak-Hing |
| author_sort | Foo, Ce Qing |
| collection | NTU |
| description | A series of PN(sp2)P ligands containing two stereogenic carbon centers were generated via the palladium(II) catalyzed asymmetric hydrophosphination of 2,6-pyridyl dienones using diphenylphosphine. Although the targeted tridentate products are powerful metal ion sequesters, poisoning of the metal catalyst due to irreversible chelation by the adducts during the course of the addition reaction was circumvented via this protocol. The reported procedure thus enabled the efficient access toward chiral PN(sp2)P pincer-type ligands in a one-pot, single-step process with good conversions and high enantioselectivities. The formed ligands can be further coordinated to various metal centers to form chiral PNP complexes with potential synthetic applications. |
| first_indexed | 2024-10-01T05:10:05Z |
| format | Journal Article |
| id | ntu-10356/160148 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T05:10:05Z |
| publishDate | 2022 |
| record_format | dspace |
| spelling | ntu-10356/1601482022-07-13T08:07:51Z Access to C-Stereogenic PN(sp²)P Pincer Ligands via Phosphapalladacycle Catalyzed Asymmetric Hydrophosphination Foo, Ce Qing Sadeer, Abdul Li, Yongxin Pullarkat, Sumod A. Leung, Pak-Hing School of Physical and Mathematical Sciences Science::Chemistry Addition Reactions Catalysis A series of PN(sp2)P ligands containing two stereogenic carbon centers were generated via the palladium(II) catalyzed asymmetric hydrophosphination of 2,6-pyridyl dienones using diphenylphosphine. Although the targeted tridentate products are powerful metal ion sequesters, poisoning of the metal catalyst due to irreversible chelation by the adducts during the course of the addition reaction was circumvented via this protocol. The reported procedure thus enabled the efficient access toward chiral PN(sp2)P pincer-type ligands in a one-pot, single-step process with good conversions and high enantioselectivities. The formed ligands can be further coordinated to various metal centers to form chiral PNP complexes with potential synthetic applications. Ministry of Education (MOE) We wish to acknowledge the research funding provided by the Singapore Ministry of Education Academic Research Fund Tier I (Grant ID 2019-T1-001-094) to support this work. 2022-07-13T08:07:51Z 2022-07-13T08:07:51Z 2021 Journal Article Foo, C. Q., Sadeer, A., Li, Y., Pullarkat, S. A. & Leung, P. (2021). Access to C-Stereogenic PN(sp²)P Pincer Ligands via Phosphapalladacycle Catalyzed Asymmetric Hydrophosphination. Organometallics, 40(6), 682-692. https://dx.doi.org/10.1021/acs.organomet.0c00783 0276-7333 https://hdl.handle.net/10356/160148 10.1021/acs.organomet.0c00783 2-s2.0-85103460451 6 40 682 692 en 2019-T1-001-094 Organometallics © 2021 American Chemical Society. All rights reserved. |
| spellingShingle | Science::Chemistry Addition Reactions Catalysis Foo, Ce Qing Sadeer, Abdul Li, Yongxin Pullarkat, Sumod A. Leung, Pak-Hing Access to C-Stereogenic PN(sp²)P Pincer Ligands via Phosphapalladacycle Catalyzed Asymmetric Hydrophosphination |
| title | Access to C-Stereogenic PN(sp²)P Pincer Ligands via Phosphapalladacycle Catalyzed Asymmetric Hydrophosphination |
| title_full | Access to C-Stereogenic PN(sp²)P Pincer Ligands via Phosphapalladacycle Catalyzed Asymmetric Hydrophosphination |
| title_fullStr | Access to C-Stereogenic PN(sp²)P Pincer Ligands via Phosphapalladacycle Catalyzed Asymmetric Hydrophosphination |
| title_full_unstemmed | Access to C-Stereogenic PN(sp²)P Pincer Ligands via Phosphapalladacycle Catalyzed Asymmetric Hydrophosphination |
| title_short | Access to C-Stereogenic PN(sp²)P Pincer Ligands via Phosphapalladacycle Catalyzed Asymmetric Hydrophosphination |
| title_sort | access to c stereogenic pn sp² p pincer ligands via phosphapalladacycle catalyzed asymmetric hydrophosphination |
| topic | Science::Chemistry Addition Reactions Catalysis |
| url | https://hdl.handle.net/10356/160148 |
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