P,N-Type benzimidazolyl phosphine ligands for the palladium-catalyzed Suzuki coupling of potassium aryltrifluoroborates and aryl chlorides

Shun Man Wong; Chau Ming So; Kin Ho Chung; Chi Him Luk; Chak Po Lau; Fuk Yee Kwong

doi:10.1016/j.tetlet.2012.05.017

P,N-Type benzimidazolyl phosphine ligands for the palladium-catalyzed Suzuki coupling of potassium aryltrifluoroborates and aryl chlorides

Shun Man Wong
, Chau Ming So
, Kin Ho Chung
, Chi Him Luk
, Chak Po Lau
, Fuk Yee Kwong

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

26 Citations (Scopus)

Abstract

This study describes the efficacy of P,N-type benzimidazolyl phosphine ligands, which can be easily synthesized from commercially available and inexpensive starting materials. The application of this ligand array in palladium-catalyzed Suzuki-Miyaura coupling reaction of aryl chlorides with potassium aryltrifluoroborates is described. The air stable benzimidazolyl phosphines in combination with a palladium metal precursor provides highly effective catalysts for the Suzuki-Miyaura coupling of unactivated aryl chlorides and can achieve a catalyst loading of only 0.05 mol %.

Original language	English
Pages (from-to)	3754-3757
Number of pages	4
Journal	Tetrahedron Letters
Volume	53
Issue number	29
DOIs	https://doi.org/10.1016/j.tetlet.2012.05.017
Publication status	Published - 18 Jul 2012
Externally published	Yes

Keywords

P,N-Type ligand
Palladium
Phosphine
Suzuki coupling
Trifluoroborate

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10.1016/j.tetlet.2012.05.017

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@article{bdd5cf51cdb14059b6cd8bfef496f452,

title = "P,N-Type benzimidazolyl phosphine ligands for the palladium-catalyzed Suzuki coupling of potassium aryltrifluoroborates and aryl chlorides",

abstract = "This study describes the efficacy of P,N-type benzimidazolyl phosphine ligands, which can be easily synthesized from commercially available and inexpensive starting materials. The application of this ligand array in palladium-catalyzed Suzuki-Miyaura coupling reaction of aryl chlorides with potassium aryltrifluoroborates is described. The air stable benzimidazolyl phosphines in combination with a palladium metal precursor provides highly effective catalysts for the Suzuki-Miyaura coupling of unactivated aryl chlorides and can achieve a catalyst loading of only 0.05 mol \%.",

keywords = "P,N-Type ligand, Palladium, Phosphine, Suzuki coupling, Trifluoroborate",

author = "Wong, \{Shun Man\} and So, \{Chau Ming\} and Chung, \{Kin Ho\} and Luk, \{Chi Him\} and Lau, \{Chak Po\} and Kwong, \{Fuk Yee\}",

note = "Funding Information: We thank the Research Grants Council of Hong Kong (GRF: PolyU 5010/11P), PolyU Internal Competitive Research Grant (A-PG13) and the University Grants Committee Areas of Excellence Scheme (AoE/P-10/01) for their financial support. We are grateful to Professor Albert S. C. Chan{\textquoteright}s research group (PolyU Hong Kong) for kindly sharing their GC instruments. ",

year = "2012",

month = jul,

day = "18",

doi = "10.1016/j.tetlet.2012.05.017",

language = "English",

volume = "53",

pages = "3754--3757",

number = "29",

}

TY - JOUR

T1 - P,N-Type benzimidazolyl phosphine ligands for the palladium-catalyzed Suzuki coupling of potassium aryltrifluoroborates and aryl chlorides

AU - Wong, Shun Man

AU - So, Chau Ming

AU - Chung, Kin Ho

AU - Luk, Chi Him

AU - Lau, Chak Po

AU - Kwong, Fuk Yee

N1 - Funding Information: We thank the Research Grants Council of Hong Kong (GRF: PolyU 5010/11P), PolyU Internal Competitive Research Grant (A-PG13) and the University Grants Committee Areas of Excellence Scheme (AoE/P-10/01) for their financial support. We are grateful to Professor Albert S. C. Chan’s research group (PolyU Hong Kong) for kindly sharing their GC instruments.

PY - 2012/7/18

Y1 - 2012/7/18

N2 - This study describes the efficacy of P,N-type benzimidazolyl phosphine ligands, which can be easily synthesized from commercially available and inexpensive starting materials. The application of this ligand array in palladium-catalyzed Suzuki-Miyaura coupling reaction of aryl chlorides with potassium aryltrifluoroborates is described. The air stable benzimidazolyl phosphines in combination with a palladium metal precursor provides highly effective catalysts for the Suzuki-Miyaura coupling of unactivated aryl chlorides and can achieve a catalyst loading of only 0.05 mol %.

AB - This study describes the efficacy of P,N-type benzimidazolyl phosphine ligands, which can be easily synthesized from commercially available and inexpensive starting materials. The application of this ligand array in palladium-catalyzed Suzuki-Miyaura coupling reaction of aryl chlorides with potassium aryltrifluoroborates is described. The air stable benzimidazolyl phosphines in combination with a palladium metal precursor provides highly effective catalysts for the Suzuki-Miyaura coupling of unactivated aryl chlorides and can achieve a catalyst loading of only 0.05 mol %.

KW - P,N-Type ligand

KW - Palladium

KW - Phosphine

KW - Suzuki coupling

KW - Trifluoroborate

UR - https://www.scopus.com/pages/publications/84862187104

U2 - 10.1016/j.tetlet.2012.05.017

DO - 10.1016/j.tetlet.2012.05.017

M3 - Article

AN - SCOPUS:84862187104

SN - 0040-4039

VL - 53

SP - 3754

EP - 3757

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 29

ER -

P,N-Type benzimidazolyl phosphine ligands for the palladium-catalyzed Suzuki coupling of potassium aryltrifluoroborates and aryl chlorides

Abstract

Keywords

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