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

doi:10.3724/SP.J.1095.2014.40064

Chinese Journal of Applied Chemistry

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

GUAN Jing^1,2, WU Guojie³, HAN Fushe^1*

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

Received:2014-03-06 Revised:2014-04-18 Published:2014-10-09 Online:2014-10-09

Abstract

Abstract: 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.

Key words: palladium, C&, mdash, H functionalization, phosphinamide, arylation, derivatization

CLC Number:

O621.2

GUAN Jing1,2, WU Guojie3, HAN Fushe1*. 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, DOI: 10.3724/SP.J.1095.2014.40064.

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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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