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PN-杂环膦配体的结构与合成

Architecture and synthesis of PN-heterocyclic phosphine ligands.

作者信息

Munzeiwa Wisdom A, Omondi Bernard, Nyamori Vincent O

机构信息

School of Chemistry and Physics, University of KwaZulu-Natal, Westville Campus, Private Bag X54001, Durban 4000, South Africa.

School of Chemistry and Physics, University of KwaZulu-Natal, Pietermaritzburg Campus, Private Bag X01, Scottsville, Pietermaritzburg 3201, South Africa.

出版信息

Beilstein J Org Chem. 2020 Mar 12;16:362-383. doi: 10.3762/bjoc.16.35. eCollection 2020.

DOI:10.3762/bjoc.16.35
PMID:32256853
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7082614/
Abstract

Diverse P,N-phosphine ligands reported to date have performed exceptionally well as auxiliary ligands in organometallic catalysis. Phosphines bearing 2-pyridyl moieties prominently feature in literature as compared to phosphines with five-membered N-heterocycles. This discussion seeks to paint a broad picture and consolidate different synthetic protocols and techniques for N-heterocyclic phosphine motifs. The introduction provides an account of P,N-phosphine ligands, and their structural and coordination benefits from combining heteroatoms with different basicity in one ligand. The body discusses the synthetic protocols which focus on P-C, P-N-bond formation, substrate and nucleophile types and different N-heterocycle construction strategies. Selected references are given in relation to the applications of the ligands.

摘要

迄今为止报道的各种P,N-膦配体在有机金属催化中作为辅助配体表现得非常出色。与带有五元N-杂环的膦相比,带有2-吡啶基部分的膦在文献中尤为突出。本讨论旨在描绘一幅广阔的图景,并整合用于N-杂环膦基序的不同合成方案和技术。引言部分介绍了P,N-膦配体,以及在一个配体中结合不同碱性杂原子所带来的结构和配位优势。正文部分讨论了合成方案,重点是P-C、P-N键的形成、底物和亲核试剂类型以及不同的N-杂环构建策略。还给出了与这些配体应用相关的参考文献。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d36b/7082614/b03c788220ac/Beilstein_J_Org_Chem-16-362-g021.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d36b/7082614/ae26f9c526d3/Beilstein_J_Org_Chem-16-362-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d36b/7082614/309b32ed8193/Beilstein_J_Org_Chem-16-362-g011.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d36b/7082614/19af5d2bf681/Beilstein_J_Org_Chem-16-362-g016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d36b/7082614/fa46c2236b94/Beilstein_J_Org_Chem-16-362-g017.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d36b/7082614/73c0eb81558c/Beilstein_J_Org_Chem-16-362-g018.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d36b/7082614/7c8daf5d8789/Beilstein_J_Org_Chem-16-362-g019.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d36b/7082614/bc865e18bebb/Beilstein_J_Org_Chem-16-362-g020.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d36b/7082614/b03c788220ac/Beilstein_J_Org_Chem-16-362-g021.jpg

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本文引用的文献

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2
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Dalton Trans. 2016 Feb 7;45(5):2237-49. doi: 10.1039/c5dt03994k. Epub 2015 Nov 24.
3
Bulky N-Phosphino-Functionalized N-Heterocyclic Carbene Ligands: Synthesis, Ruthenium Coordination Chemistry, and Ruthenium Alkylidene Complexes for Olefin Metathesis.
Molecules. 2022 Sep 23;27(19):6293. doi: 10.3390/molecules27196293.
4
Coinage Metal Complexes of Bis(quinoline-2-ylmethyl)phenylphosphine-Simple Reactions Can Lead to Unprecedented Results.双(喹啉-2-基甲基)苯基膦的硬币金属配合物——简单反应可产生前所未有的结果。
ChemistryOpen. 2022 Mar;11(3):e202100224. doi: 10.1002/open.202100224. Epub 2022 Feb 10.
大位阻N-膦基官能化N-杂环卡宾配体:合成、钌配位化学及用于烯烃复分解反应的钌亚烷基配合物
Inorg Chem. 2015 Nov 2;54(21):10126-40. doi: 10.1021/acs.inorgchem.5b00513. Epub 2015 Oct 19.
4
Enantioselective synthesis of tunable chiral Clickphine P,N-ligands and their application in Ir-catalyzed asymmetric hydrogenation.可调谐手性Clickphine P,N配体的对映选择性合成及其在铱催化不对称氢化反应中的应用。
J Org Chem. 2015 Apr 3;80(7):3634-42. doi: 10.1021/acs.joc.5b00438. Epub 2015 Mar 16.
5
Pd-catalyzed asymmetric allylic amination using easily accessible metallocenyl P,N-ligands.使用易于获得的茂金属P,N配体的钯催化不对称烯丙基胺化反应。
Org Biomol Chem. 2015 Apr 14;13(14):4248-54. doi: 10.1039/c5ob00032g. Epub 2015 Mar 6.
6
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7
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8
Zinc and cobalt complexes based on tripodal ligands: synthesis, structure and reactivity toward lactide.基于三脚架配体的锌和钴配合物:合成、结构及对丙交酯的反应性。
Dalton Trans. 2014 Mar 21;43(11):4550-64. doi: 10.1039/c3dt52629a.
9
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