Synthesis of Chiral-Bridged Atropisomeric Monophosphine Ligands with Tunable Dihedral Angles and their Applications in Asymmetric Suzuki–Miyaura Coupling Reactions

Wang Xia; Yongsu Li; Zihong Zhou; Huixuan Chen; Hao Liang; Sifan Yu; Xuefeng He; Yaqi Zhang; Jiyan Pang; Zhongyuan Zhou; Liqin Qiu

doi:10.1002/adsc.201700020

Synthesis of Chiral-Bridged Atropisomeric Monophosphine Ligands with Tunable Dihedral Angles and their Applications in Asymmetric Suzuki–Miyaura Coupling Reactions

Wang Xia, Yongsu Li, Zihong Zhou, Huixuan Chen, Hao Liang, Sifan Yu, Xuefeng He, Yaqi Zhang, Jiyan Pang, Zhongyuan Zhou, Liqin Qiu^*

^*Corresponding author for this work

Chinese Medicine - Teaching and Research Division

Research output: Contribution to journal › Journal article › peer-review

29 Citations (Scopus)

Abstract

Precise chiral recognition was firstly realized in the construction of diastereomeric biaryl monophosphines by means of the substrate-directed asymmetric annulation reactions. A series of new chiral-bridged atropisomeric biphenyl monophosphine ligands with tunable dihedral angles was accordingly synthesized successfully without a resolution step being needed. Using these ligands, different kinds of axially chiral 1,1′-biaryl-2-phosphonates including the first reported quinolyl biaryl phosphonates were prepared in 42–97% yields with up to 96% ee via palladium-catalyzed asymmetric Suzuki coupling reactions.

Original language	English
Pages (from-to)	1656-1662
Number of pages	7
Journal	Advanced Synthesis and Catalysis
Volume	359
Issue number	10
Early online date	15 Mar 2017
DOIs	https://doi.org/10.1002/adsc.201700020
Publication status	Published - 17 May 2017

User-Defined Keywords

asymmetric catalysis
diastereoselective synthesis
heterocyclic biaryls
monophosphine ligands
quinoline derivatives
Suzuki coupling

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1002/adsc.201700020

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Xia, W., Li, Y., Zhou, Z., Chen, H., Liang, H., Yu, S., He, X., Zhang, Y., Pang, J., Zhou, Z., & Qiu, L. (2017). Synthesis of Chiral-Bridged Atropisomeric Monophosphine Ligands with Tunable Dihedral Angles and their Applications in Asymmetric Suzuki–Miyaura Coupling Reactions. Advanced Synthesis and Catalysis, 359(10), 1656-1662. https://doi.org/10.1002/adsc.201700020

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title = "Synthesis of Chiral-Bridged Atropisomeric Monophosphine Ligands with Tunable Dihedral Angles and their Applications in Asymmetric Suzuki–Miyaura Coupling Reactions",

abstract = "Precise chiral recognition was firstly realized in the construction of diastereomeric biaryl monophosphines by means of the substrate-directed asymmetric annulation reactions. A series of new chiral-bridged atropisomeric biphenyl monophosphine ligands with tunable dihedral angles was accordingly synthesized successfully without a resolution step being needed. Using these ligands, different kinds of axially chiral 1,1′-biaryl-2-phosphonates including the first reported quinolyl biaryl phosphonates were prepared in 42–97% yields with up to 96% ee via palladium-catalyzed asymmetric Suzuki coupling reactions.",

keywords = "asymmetric catalysis, diastereoselective synthesis, heterocyclic biaryls, monophosphine ligands, quinoline derivatives, Suzuki coupling",

author = "Wang Xia and Yongsu Li and Zihong Zhou and Huixuan Chen and Hao Liang and Sifan Yu and Xuefeng He and Yaqi Zhang and Jiyan Pang and Zhongyuan Zhou and Liqin Qiu",

note = "National Natural Science Foundation of China (NSFCC). Grant Number: 21272283 Special Financial Fund of Innovative Development of Marine Economic Demonstration Project. Grant Number: GD2012-D01-001 Guangdong Provincial Natural Science Foundation. Grant Number: S2011010001305 Dayawan District Science and Technology Program. Grant Number: 201202002 Publisher Copyright: {\textcopyright} 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2017",

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doi = "10.1002/adsc.201700020",

language = "English",

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Xia, W, Li, Y, Zhou, Z, Chen, H, Liang, H, Yu, S, He, X, Zhang, Y, Pang, J, Zhou, Z & Qiu, L 2017, 'Synthesis of Chiral-Bridged Atropisomeric Monophosphine Ligands with Tunable Dihedral Angles and their Applications in Asymmetric Suzuki–Miyaura Coupling Reactions', Advanced Synthesis and Catalysis, vol. 359, no. 10, pp. 1656-1662. https://doi.org/10.1002/adsc.201700020

TY - JOUR

T1 - Synthesis of Chiral-Bridged Atropisomeric Monophosphine Ligands with Tunable Dihedral Angles and their Applications in Asymmetric Suzuki–Miyaura Coupling Reactions

AU - Xia, Wang

AU - Li, Yongsu

AU - Zhou, Zihong

AU - Chen, Huixuan

AU - Liang, Hao

AU - Yu, Sifan

AU - He, Xuefeng

AU - Zhang, Yaqi

AU - Pang, Jiyan

AU - Zhou, Zhongyuan

AU - Qiu, Liqin

N1 - National Natural Science Foundation of China (NSFCC). Grant Number: 21272283 Special Financial Fund of Innovative Development of Marine Economic Demonstration Project. Grant Number: GD2012-D01-001 Guangdong Provincial Natural Science Foundation. Grant Number: S2011010001305 Dayawan District Science and Technology Program. Grant Number: 201202002 Publisher Copyright: © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2017/5/17

Y1 - 2017/5/17

N2 - Precise chiral recognition was firstly realized in the construction of diastereomeric biaryl monophosphines by means of the substrate-directed asymmetric annulation reactions. A series of new chiral-bridged atropisomeric biphenyl monophosphine ligands with tunable dihedral angles was accordingly synthesized successfully without a resolution step being needed. Using these ligands, different kinds of axially chiral 1,1′-biaryl-2-phosphonates including the first reported quinolyl biaryl phosphonates were prepared in 42–97% yields with up to 96% ee via palladium-catalyzed asymmetric Suzuki coupling reactions.

AB - Precise chiral recognition was firstly realized in the construction of diastereomeric biaryl monophosphines by means of the substrate-directed asymmetric annulation reactions. A series of new chiral-bridged atropisomeric biphenyl monophosphine ligands with tunable dihedral angles was accordingly synthesized successfully without a resolution step being needed. Using these ligands, different kinds of axially chiral 1,1′-biaryl-2-phosphonates including the first reported quinolyl biaryl phosphonates were prepared in 42–97% yields with up to 96% ee via palladium-catalyzed asymmetric Suzuki coupling reactions.

KW - asymmetric catalysis

KW - diastereoselective synthesis

KW - heterocyclic biaryls

KW - monophosphine ligands

KW - quinoline derivatives

KW - Suzuki coupling

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U2 - 10.1002/adsc.201700020

DO - 10.1002/adsc.201700020

M3 - Journal article

AN - SCOPUS:85015231320

SN - 1615-4150

VL - 359

SP - 1656

EP - 1662

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 10

ER -

Synthesis of Chiral-Bridged Atropisomeric Monophosphine Ligands with Tunable Dihedral Angles and their Applications in Asymmetric Suzuki–Miyaura Coupling Reactions

Abstract

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