Palladium-Catalyzed Cs2CO3-Promoted Arylation of Unactivated C(sp3)-H Bonds by (Diacetoxyiodo)arenes: Shifting the Reactivity of (Diacetoxyiodo)arenes from Acetoxylation to Arylation

被引：44

作者：

Gou, Quan ^{[1
]}

Zhang, Zhao-Fu ^{[1
]}

Liu, Zhi-Cheng ^{[1
]}

Qin, Jun ^{[1
]}

机构：

[1] Yunnan Univ, Sch Chem Sci & Technol, Key Lab Med Chem Nat Resource, Minist Educ, Kunming 650091, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 06期

基金：

中国国家自然科学基金;

关键词：

C-H BONDS; DIRECTING GROUP; STEREOSELECTIVE-SYNTHESIS; INTERMOLECULAR ARYLATION; COUPLING REACTIONS; FUNCTIONALIZATION; ACTIVATION; CARBON; ALKYLATION; SP(2);

D O I：

10.1021/acs.joc.5b00111

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

PdCl2(CH3CN)(2)-catalyzed arylation of unactivated C(sp(3))-H bonds using (diacetoxyiodo)arenes as arylation reagents is reported. The reactivity of (diacetoxyiodo)arenes as arylation reagents is enabled in the presence of Cs2CO3 under the reaction conditions. This arylation method is highly efficient and occurs without the use of silver salt. The reaction tolerates a broad substrate scope that was not demonstrated by other silver salt-free C(sp(3))-H bond arylation conditions. The synthetic utility of the method is further illustrated in the synthesis of the psychotropic drug phenibut. A detailed mechanism study has been conducted to understand the reaction pathway.

引用

页码：3176 / 3186

页数：11

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