Nickel-Catalyzed Asymmetric C(sp2)-P Coupling for the Direct Synthesis of the PMOP Atropisomeric Phosphine Ligand

Bendu Pan; Mingliang Li; Zhiping Yang; Jun Wang

doi:10.1021/acs.orglett.6c03015

Nickel-Catalyzed Asymmetric C(sp2)-P Coupling for the Direct Synthesis of the PMOP Atropisomeric Phosphine Ligand

Bendu Pan
, Mingliang Li
, Zhiping Yang^*
, Jun Wang^*

^*Corresponding author for this work

Department of Chemistry

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

Abstract

An efficient kinetic resolution of binaphthyl triflates is developed via Ni-catalyzed asymmetric C(sp2)-P cross-coupling to access substituted atropisomeric phosphines. Moreover, the phosphine framework showed superior reactivity and enantiocontrol in Pd-catalyzed asymmetric allylic substitution. Mechanistic control experiments revealed that the introduction of a pyridine ring provides both optimal steric hindrance and a secondary coordination site, enabling the successful development of a new class of atropisomeric P,N-bidentate ligands, denoted as PMOP.

Original language	English
Pages (from-to)	10785-10790
Number of pages	6
Journal	Organic Letters
Volume	28
Issue number	34
Early online date	14 Aug 2026
DOIs	https://doi.org/10.1021/acs.orglett.6c03015
Publication status	Published - 28 Aug 2026

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10.1021/acs.orglett.6c03015

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title = "Nickel-Catalyzed Asymmetric C(sp2)-P Coupling for the Direct Synthesis of the PMOP Atropisomeric Phosphine Ligand",

abstract = "An efficient kinetic resolution of binaphthyl triflates is developed via Ni-catalyzed asymmetric C(sp2)-P cross-coupling to access substituted atropisomeric phosphines. Moreover, the phosphine framework showed superior reactivity and enantiocontrol in Pd-catalyzed asymmetric allylic substitution. Mechanistic control experiments revealed that the introduction of a pyridine ring provides both optimal steric hindrance and a secondary coordination site, enabling the successful development of a new class of atropisomeric P,N-bidentate ligands, denoted as PMOP.",

author = "Bendu Pan and Mingliang Li and Zhiping Yang and Jun Wang",

note = "The authors gratefully acknowledge the University Grants Committee (Hong Kong) (GRF 12302825 and SRFS2526-2S02), the National Natural Science Foundation of China (NSFC 22271241), and HKBU RC-SFCRG/23-24 for financial support. Z.Y. acknowledges the K. C. Wong Education Foundation. The authors acknowledge the facility support from the Advanced Life Sciences and Mass Spectrometry Laboratory (LSMS) of Hong Kong Baptist University. Publisher Copyright: {\textcopyright} 2026 American Chemical Society.",

year = "2026",

month = aug,

day = "28",

doi = "10.1021/acs.orglett.6c03015",

language = "English",

volume = "28",

pages = "10785--10790",

journal = "Organic Letters",

issn = "1523-7060",

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T1 - Nickel-Catalyzed Asymmetric C(sp2)-P Coupling for the Direct Synthesis of the PMOP Atropisomeric Phosphine Ligand

AU - Pan, Bendu

AU - Li, Mingliang

AU - Yang, Zhiping

AU - Wang, Jun

N1 - The authors gratefully acknowledge the University Grants Committee (Hong Kong) (GRF 12302825 and SRFS2526-2S02), the National Natural Science Foundation of China (NSFC 22271241), and HKBU RC-SFCRG/23-24 for financial support. Z.Y. acknowledges the K. C. Wong Education Foundation. The authors acknowledge the facility support from the Advanced Life Sciences and Mass Spectrometry Laboratory (LSMS) of Hong Kong Baptist University. Publisher Copyright: © 2026 American Chemical Society.

PY - 2026/8/28

Y1 - 2026/8/28

N2 - An efficient kinetic resolution of binaphthyl triflates is developed via Ni-catalyzed asymmetric C(sp2)-P cross-coupling to access substituted atropisomeric phosphines. Moreover, the phosphine framework showed superior reactivity and enantiocontrol in Pd-catalyzed asymmetric allylic substitution. Mechanistic control experiments revealed that the introduction of a pyridine ring provides both optimal steric hindrance and a secondary coordination site, enabling the successful development of a new class of atropisomeric P,N-bidentate ligands, denoted as PMOP.

AB - An efficient kinetic resolution of binaphthyl triflates is developed via Ni-catalyzed asymmetric C(sp2)-P cross-coupling to access substituted atropisomeric phosphines. Moreover, the phosphine framework showed superior reactivity and enantiocontrol in Pd-catalyzed asymmetric allylic substitution. Mechanistic control experiments revealed that the introduction of a pyridine ring provides both optimal steric hindrance and a secondary coordination site, enabling the successful development of a new class of atropisomeric P,N-bidentate ligands, denoted as PMOP.

UR - https://www.scopus.com/pages/publications/105048925406

UR - https://pubs.acs.org/orlef7/article/28/34/10785/5257681/Nickel-Catalyzed-Asymmetric-C-sp2-P-Coupling-for

U2 - 10.1021/acs.orglett.6c03015

DO - 10.1021/acs.orglett.6c03015

M3 - Journal article

C2 - 42681774

AN - SCOPUS:105048925406

SN - 1523-7060

VL - 28

SP - 10785

EP - 10790

JO - Organic Letters

JF - Organic Letters

IS - 34

ER -

Nickel-Catalyzed Asymmetric C(sp2)-P Coupling for the Direct Synthesis of the PMOP Atropisomeric Phosphine Ligand

Abstract

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