Promotion Mechanism of H2O for Stereoselectivity in Pd(II)-catalyzed C—H Arylation of Diarylphosphinamides with Arylboronic Acids

doi:10.1007/s40242-019-9013-9

高等学校化学研究 ›› 2020, Vol. 36 ›› Issue (5): 843-846.doi: 10.1007/s40242-019-9013-9

Promotion Mechanism of H₂O for Stereoselectivity in Pd(II)-catalyzed C—H Arylation of Diarylphosphinamides with Arylboronic Acids

CAI Yanchun, JIAO Long, QIU Xuepeng, DU Zhijun

Polymer Composites Engineering Laboratory, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, P. R. China

收稿日期:2019-10-20 修回日期:2019-11-16 出版日期:2020-10-01 发布日期:2020-10-01
通讯作者: DU Zhijun E-mail:dzj1126@ciac.ac.cn
基金资助:
Supported by the National Natural Science Foundation of China(No.21772190).

Promotion Mechanism of H₂O for Stereoselectivity in Pd(II)-catalyzed C-H Arylation of Diarylphosphinamides with Arylboronic Acids

CAI Yanchun, JIAO Long, QIU Xuepeng, DU Zhijun

Polymer Composites Engineering Laboratory, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, P. R. China

Received:2019-10-20 Revised:2019-11-16 Online:2020-10-01 Published:2020-10-01
Contact: DU Zhijun E-mail:dzj1126@ciac.ac.cn
Supported by:
Supported by the National Natural Science Foundation of China(No.21772190).

摘要/Abstract

摘要： On the basis of a series of control experiments and nuclear magnetic resonance analyses, it is discovered that Boc-protected amino acid ligand coordinated to Pd center is partly replaced by N,N-dimethylformamide, and H₂O can inhibit coordination of N,N-dimethylformamide to Pd center. The novel action mechanism perfectly explains H₂O promotion for stereoselectivity in Pd(II)-catalyzed C—H arylation of diarylphosphinamides with arylboronic acids.

关键词: C—H activation, Stereoselectivity, Water, Ligand exchange

Abstract: On the basis of a series of control experiments and nuclear magnetic resonance analyses, it is discovered that Boc-protected amino acid ligand coordinated to Pd center is partly replaced by N,N-dimethylformamide, and H₂O can inhibit coordination of N,N-dimethylformamide to Pd center. The novel action mechanism perfectly explains H₂O promotion for stereoselectivity in Pd(II)-catalyzed C-H arylation of diarylphosphinamides with arylboronic acids.

Key words: C-H activation, Stereoselectivity, Water, Ligand exchange

CAI Yanchun, JIAO Long, QIU Xuepeng, DU Zhijun. Promotion Mechanism of H₂O for Stereoselectivity in Pd(II)-catalyzed C—H Arylation of Diarylphosphinamides with Arylboronic Acids[J]. 高等学校化学研究, 2020, 36(5): 843-846.

CAI Yanchun, JIAO Long, QIU Xuepeng, DU Zhijun. Promotion Mechanism of H₂O for Stereoselectivity in Pd(II)-catalyzed C-H Arylation of Diarylphosphinamides with Arylboronic Acids[J]. Chemical Research in Chinese Universities, 2020, 36(5): 843-846.

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Promotion Mechanism of H₂O for Stereoselectivity in Pd(II)-catalyzed C—H Arylation of Diarylphosphinamides with Arylboronic Acids

Promotion Mechanism of H₂O for Stereoselectivity in Pd(II)-catalyzed C-H Arylation of Diarylphosphinamides with Arylboronic Acids

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