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镍催化芳基卤化物的对映选择性交叉亲电偶联:一种合成多种MOP型配体的通用实用方法。

Nickel-Catalyzed Atroposelective Cross-Electrophile Coupling of Aryl Halides: A General and Practical Route to Diverse MOP-Type Ligands.

作者信息

Kim Raphael S, Kgoadi Lebogang O, Hayes Jacob C, Rainboth Derek P, Mudd Catherine M, Yap Glenn P A, Watson Donald A

机构信息

Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, United States.

出版信息

J Am Chem Soc. 2024 Jul 3;146(26):17606-17612. doi: 10.1021/jacs.4c04608. Epub 2024 May 23.

DOI:10.1021/jacs.4c04608
PMID:38780663
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11222061/
Abstract

We report a highly cross- and atroposelective coupling between -(chloro)arylphosphine oxides and -(bromo)aryl ethers. This previously unknown asymmetric nickel-catalyzed reaction offers a direct route to highly enantioenriched axially chiral biaryl monophosphine oxides that are difficult to access by other means. These products can be readily reduced to generate chiral MOP-type ligands bearing complex skeletal backbones. The utility of these chiral ligands in asymmetric catalysis is also demonstrated.

摘要

我们报道了一种在(氯)芳基氧化膦和(溴)芳基醚之间进行的高度交叉和阻转选择性偶联反应。这种此前未知的不对称镍催化反应提供了一条直接合成高度对映体富集的轴向手性联芳基单氧化膦的途径,而通过其他方法难以获得此类化合物。这些产物可以很容易地被还原以生成带有复杂骨架的手性MOP型配体。还展示了这些手性配体在不对称催化中的实用性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3003/11222061/ee4ba69277b0/nihms-1997663-f0010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3003/11222061/f59d18b3b3ec/nihms-1997663-f0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3003/11222061/00ef456924cf/nihms-1997663-f0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3003/11222061/2e078411ea24/nihms-1997663-f0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3003/11222061/205961b14f9b/nihms-1997663-f0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3003/11222061/ee4ba69277b0/nihms-1997663-f0010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3003/11222061/f59d18b3b3ec/nihms-1997663-f0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3003/11222061/00ef456924cf/nihms-1997663-f0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3003/11222061/2e078411ea24/nihms-1997663-f0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3003/11222061/205961b14f9b/nihms-1997663-f0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3003/11222061/ee4ba69277b0/nihms-1997663-f0010.jpg

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