Cobalt-Catalyzed Enantioselective Hydrogenation of Diaryl Ketones with Ferrocene-Based Secondary Phosphine Oxide Ligands

Liyao Zeng; Menglong Zhao; Bijin Lin; Jingyuan Song; James H R Tucker; Jialin Wen; Xumu Zhang

doi:10.1021/acs.orglett.3c02530

Cobalt-Catalyzed Enantioselective Hydrogenation of Diaryl Ketones with Ferrocene-Based Secondary Phosphine Oxide Ligands

Liyao Zeng, Menglong Zhao, Bijin Lin, Jingyuan Song, James H R Tucker, Jialin Wen^*, Xumu Zhang^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Letter › peer-review

Abstract

A new class of cobalt catalytic system for asymmetric hydrogenation of ketones was herein reported, involving the development of novel ferrocene-based secondary phosphine oxide ligands. An unusual P-O bidentate coordination pattern with cobalt was confirmed by an X-ray diffraction study. The bichelating tetrahedral cobalt(II) complexes afforded high reactivities (up to 99% yield) and good to excellent enantioselectivities (up to 92% ee) in the AH of various ortho-substituted diaryl ketones. In addition, the diferrocenyl cobalt complex was characterized with intriguing UV-vis absorption and electrochemical properties.

Original language	English
Pages (from-to)	6228-6233
Number of pages	6
Journal	Organic letters
Volume	25
Issue number	33
Early online date	16 Aug 2023
DOIs	https://doi.org/10.1021/acs.orglett.3c02530
Publication status	Published - 25 Aug 2023

Bibliographical note

Acknowledgments:
We are grateful for Dr. Fanping Huang (Southern University of Science and Technology) for his assistance in the X-ray diffraction analysis of crystal structure. We are grateful for Jack Dismorr (University of Birmingham) for his assistance in the operation of cyclic voltammetry of the ferrocenyl compounds. This project was financially supported by National Natural Science Foundation of China (21991113), Guangdong Provincial Key Laboratory of Catalysis (2020B121201002) and the Stable Support Plan Program of Shenzhen Natural Science Fund (20200925161222002).

Access to Document

10.1021/acs.orglett.3c02530

Cite this

@article{d72c9f3745714dde9258bbec3e565b2b,

title = "Cobalt-Catalyzed Enantioselective Hydrogenation of Diaryl Ketones with Ferrocene-Based Secondary Phosphine Oxide Ligands",

abstract = "A new class of cobalt catalytic system for asymmetric hydrogenation of ketones was herein reported, involving the development of novel ferrocene-based secondary phosphine oxide ligands. An unusual P-O bidentate coordination pattern with cobalt was confirmed by an X-ray diffraction study. The bichelating tetrahedral cobalt(II) complexes afforded high reactivities (up to 99% yield) and good to excellent enantioselectivities (up to 92% ee) in the AH of various ortho-substituted diaryl ketones. In addition, the diferrocenyl cobalt complex was characterized with intriguing UV-vis absorption and electrochemical properties. ",

author = "Liyao Zeng and Menglong Zhao and Bijin Lin and Jingyuan Song and Tucker, {James H R} and Jialin Wen and Xumu Zhang",

note = "Acknowledgments: We are grateful for Dr. Fanping Huang (Southern University of Science and Technology) for his assistance in the X-ray diffraction analysis of crystal structure. We are grateful for Jack Dismorr (University of Birmingham) for his assistance in the operation of cyclic voltammetry of the ferrocenyl compounds. This project was financially supported by National Natural Science Foundation of China (21991113), Guangdong Provincial Key Laboratory of Catalysis (2020B121201002) and the Stable Support Plan Program of Shenzhen Natural Science Fund (20200925161222002).",

year = "2023",

month = aug,

day = "25",

doi = "10.1021/acs.orglett.3c02530",

language = "English",

volume = "25",

pages = "6228--6233",

journal = "Organic letters",

issn = "1523-7052",

publisher = "American Chemical Society",

number = "33",

}

TY - JOUR

T1 - Cobalt-Catalyzed Enantioselective Hydrogenation of Diaryl Ketones with Ferrocene-Based Secondary Phosphine Oxide Ligands

AU - Zeng, Liyao

AU - Zhao, Menglong

AU - Lin, Bijin

AU - Song, Jingyuan

AU - Tucker, James H R

AU - Wen, Jialin

AU - Zhang, Xumu

N1 - Acknowledgments: We are grateful for Dr. Fanping Huang (Southern University of Science and Technology) for his assistance in the X-ray diffraction analysis of crystal structure. We are grateful for Jack Dismorr (University of Birmingham) for his assistance in the operation of cyclic voltammetry of the ferrocenyl compounds. This project was financially supported by National Natural Science Foundation of China (21991113), Guangdong Provincial Key Laboratory of Catalysis (2020B121201002) and the Stable Support Plan Program of Shenzhen Natural Science Fund (20200925161222002).

PY - 2023/8/25

Y1 - 2023/8/25

N2 - A new class of cobalt catalytic system for asymmetric hydrogenation of ketones was herein reported, involving the development of novel ferrocene-based secondary phosphine oxide ligands. An unusual P-O bidentate coordination pattern with cobalt was confirmed by an X-ray diffraction study. The bichelating tetrahedral cobalt(II) complexes afforded high reactivities (up to 99% yield) and good to excellent enantioselectivities (up to 92% ee) in the AH of various ortho-substituted diaryl ketones. In addition, the diferrocenyl cobalt complex was characterized with intriguing UV-vis absorption and electrochemical properties.

AB - A new class of cobalt catalytic system for asymmetric hydrogenation of ketones was herein reported, involving the development of novel ferrocene-based secondary phosphine oxide ligands. An unusual P-O bidentate coordination pattern with cobalt was confirmed by an X-ray diffraction study. The bichelating tetrahedral cobalt(II) complexes afforded high reactivities (up to 99% yield) and good to excellent enantioselectivities (up to 92% ee) in the AH of various ortho-substituted diaryl ketones. In addition, the diferrocenyl cobalt complex was characterized with intriguing UV-vis absorption and electrochemical properties.

U2 - 10.1021/acs.orglett.3c02530

DO - 10.1021/acs.orglett.3c02530

M3 - Letter

C2 - 37585346

SN - 1523-7052

VL - 25

SP - 6228

EP - 6233

JO - Organic letters

JF - Organic letters

IS - 33

ER -

Cobalt-Catalyzed Enantioselective Hydrogenation of Diaryl Ketones with Ferrocene-Based Secondary Phosphine Oxide Ligands

Abstract

Bibliographical note

Access to Document

Fingerprint

Cite this