Pyridine-promoted diazotization of P[sbnd]H bonds with aryl diazonium tetrafluoroborates: Synthesis of azo organophosphorus compounds

Fan Cao; Lulu Si; Shipan Xu; Longzhi Zhu; Yu Liu; Weifeng Xu; Ke Wen Tang; Biquan Xiong; Wai Yeung Wong

doi:10.1016/j.tetlet.2022.154207

Pyridine-promoted diazotization of P[sbnd]H bonds with aryl diazonium tetrafluoroborates: Synthesis of azo organophosphorus compounds

Fan Cao
, Lulu Si
, Shipan Xu
, Longzhi Zhu
, Yu Liu
, Weifeng Xu
, Ke Wen Tang
, Biquan Xiong
, Wai Yeung Wong (Corresponding Author)

Research output: Journal article publication › Journal article › Academic research › peer-review

3 Citations (Scopus)

Abstract

A pyridine-promoted diazotization of P[sbnd]H bonds with aryl diazonium tetrafluoroborates is established. The reported method is simple and efficient for the synthesis of azo organophosphorus compounds with excellent yields, which avoids the adoption of complex and harsh reaction conditions and the addition of oxides, tolerating various kinds of functional groups. The synthesized azo organophosphorus compounds may have potential applications in organic chemistry and drug design.

Original language	English
Article number	154207
Journal	Tetrahedron Letters
Volume	111
DOIs	https://doi.org/10.1016/j.tetlet.2022.154207
Publication status	Published - 23 Nov 2022

Keywords

Aryl diazonium tetrafluoroborates
Diazotization reaction
P[sbnd]H bonds
Transition-metal free synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

More information

10.1016/j.tetlet.2022.154207

Cite this

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title = "Pyridine-promoted diazotization of P[sbnd]H bonds with aryl diazonium tetrafluoroborates: Synthesis of azo organophosphorus compounds",

abstract = "A pyridine-promoted diazotization of P[sbnd]H bonds with aryl diazonium tetrafluoroborates is established. The reported method is simple and efficient for the synthesis of azo organophosphorus compounds with excellent yields, which avoids the adoption of complex and harsh reaction conditions and the addition of oxides, tolerating various kinds of functional groups. The synthesized azo organophosphorus compounds may have potential applications in organic chemistry and drug design.",

keywords = "Aryl diazonium tetrafluoroborates, Diazotization reaction, P[sbnd]H bonds, Transition-metal free synthesis",

author = "Fan Cao and Lulu Si and Shipan Xu and Longzhi Zhu and Yu Liu and Weifeng Xu and Tang, \{Ke Wen\} and Biquan Xiong and Wong, \{Wai Yeung\}",

note = "Funding Information: This work was supported by the National Natural Science Foundation of China (21606080, 21908050), Open Project of Hunan Provincial Key Laboratory (HNPCCS201905), Scientific Research Fund of the Hunan Provincial Education Department (19B246), and Innovation Research Group Project of the Natural Science Foundation of Hunan Province (No. 2020JJ1004). W.-Y.W. thanks the CAS-Croucher Funding Scheme for Joint Laboratories, ITC Guangdong-Hong Kong Technology Cooperation Funding Scheme (TCFS) (GHP/038/19GD), RGC Senior Research Fellowship Scheme (SRFS 2021-5S01), Research Institute for Smart Energy (CDAQ) and the Endowed Professorship in Energy from Miss Clarea Au (847S) for financial support. Publisher Copyright: {\textcopyright} 2022 Elsevier Ltd",

year = "2022",

month = nov,

day = "23",

doi = "10.1016/j.tetlet.2022.154207",

language = "English",

volume = "111",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

}

TY - JOUR

T1 - Pyridine-promoted diazotization of P[sbnd]H bonds with aryl diazonium tetrafluoroborates

T2 - Synthesis of azo organophosphorus compounds

AU - Cao, Fan

AU - Si, Lulu

AU - Xu, Shipan

AU - Zhu, Longzhi

AU - Liu, Yu

AU - Xu, Weifeng

AU - Tang, Ke Wen

AU - Xiong, Biquan

AU - Wong, Wai Yeung

N1 - Funding Information: This work was supported by the National Natural Science Foundation of China (21606080, 21908050), Open Project of Hunan Provincial Key Laboratory (HNPCCS201905), Scientific Research Fund of the Hunan Provincial Education Department (19B246), and Innovation Research Group Project of the Natural Science Foundation of Hunan Province (No. 2020JJ1004). W.-Y.W. thanks the CAS-Croucher Funding Scheme for Joint Laboratories, ITC Guangdong-Hong Kong Technology Cooperation Funding Scheme (TCFS) (GHP/038/19GD), RGC Senior Research Fellowship Scheme (SRFS 2021-5S01), Research Institute for Smart Energy (CDAQ) and the Endowed Professorship in Energy from Miss Clarea Au (847S) for financial support. Publisher Copyright: © 2022 Elsevier Ltd

PY - 2022/11/23

Y1 - 2022/11/23

N2 - A pyridine-promoted diazotization of P[sbnd]H bonds with aryl diazonium tetrafluoroborates is established. The reported method is simple and efficient for the synthesis of azo organophosphorus compounds with excellent yields, which avoids the adoption of complex and harsh reaction conditions and the addition of oxides, tolerating various kinds of functional groups. The synthesized azo organophosphorus compounds may have potential applications in organic chemistry and drug design.

AB - A pyridine-promoted diazotization of P[sbnd]H bonds with aryl diazonium tetrafluoroborates is established. The reported method is simple and efficient for the synthesis of azo organophosphorus compounds with excellent yields, which avoids the adoption of complex and harsh reaction conditions and the addition of oxides, tolerating various kinds of functional groups. The synthesized azo organophosphorus compounds may have potential applications in organic chemistry and drug design.

KW - Aryl diazonium tetrafluoroborates

KW - Diazotization reaction

KW - P[sbnd]H bonds

KW - Transition-metal free synthesis

UR - https://www.scopus.com/pages/publications/85141272113

U2 - 10.1016/j.tetlet.2022.154207

DO - 10.1016/j.tetlet.2022.154207

M3 - Journal article

AN - SCOPUS:85141272113

SN - 0040-4039

VL - 111

JO - Tetrahedron Letters

JF - Tetrahedron Letters

M1 - 154207

ER -

Pyridine-promoted diazotization of P[sbnd]H bonds with aryl diazonium tetrafluoroborates: Synthesis of azo organophosphorus compounds

Abstract

Keywords

ASJC Scopus subject areas

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