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Citation: GUAN Jing, WU Guojie, HAN Fushe. Pd^(Ⅱ)-Catalyzed C--H Arylation of Aryl Phosphonic Acid Derivatives and the Derivatization Reaction of the Coupled Products[J]. Chinese Journal of Applied Chemistry, ;2014, 31(11): 1280-1289. doi: 10.3724/SP.J.1095.2014.40064 shu

Pd^(Ⅱ)-Catalyzed C--H Arylation of Aryl Phosphonic Acid Derivatives and the Derivatization Reaction of the Coupled Products

GUAN Jing ^a,b ,
WU Guojie ^c ,
HAN Fushe ^a,,

1.
a Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, Jilin 130022, China;
2.
b The University of Chinese Academy of Scicences, Beijing 100864, China;
3.
c Department of Chemistry, Northeast Normal University, Changchun, Jilin 130024, China

Corresponding author: HAN Fushe,
Received Date: 6 March 2014
Available Online: 21 April 2014

The C-H arylation of various phosphinic acid derivatives was investigated.After a comprehensive screen of various reaction parameters,we found that direct C——H arylation of aryl phosphinamides could proceed effectively with Pd(OAc)₂ as catalyst,Ag₂CO₃ as oxidant,and benzoquinone(BQ) as additive in DMF.Mechanistic study revealed that the reaction proceeded via a Pd^(Ⅱ) to Pd⁽⁰⁾ cycle.Further elaboration demonstrated that arylated phosphinamides could be converted into the corresponding aryl phosphinates and H-biaryl phosphines in high efficiency,with yields of 98% and 82%,respectively.Consequently,the results presented herein would offer a new method for the synthesis of polyaryl phosphorus compounds.
- palladium,
- C-H functionalization,
- phosphinamide,
- arylation,
- derivatization
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Pd(Ⅱ)-Catalyzed C--H Arylation of Aryl Phosphonic Acid Derivatives and the Derivatization Reaction of the Coupled Products

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通讯作者: 陈斌, bchen63@163.com

Pd^(Ⅱ)-Catalyzed C--H Arylation of Aryl Phosphonic Acid Derivatives and the Derivatization Reaction of the Coupled Products