B2pin2-Mediated Palladium-Catalyzed Diacetoxylation of Aryl Alkenes with O2 as Oxygen Source and Sole Oxidant

被引：19

作者：

Huang, Jiuzhong ^{[1
]}

Ouyang, Lu ^{[1
]}

Li, Jianxiao ^{[1
]}

Zheng, Jia ^{[1
]}

Yan, Wuxin ^{[1
]}

Wu, Wanqing ^{[1
]}

Jiang, Huanfeng ^{[1
]}

机构：

[1] South China Univ Technol, Sch Chem & Chem Engn, Key Lab Funct Mol Engn Guangdong Prov, Guangzhou 510640, Guangdong, Peoples R China

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 17期

基金：

中国国家自然科学基金;

关键词：

ELECTROPHILIC DISPLACEMENT-REACTIONS; MOLECULAR-OXYGEN; HYDROGEN-PEROXIDE; REDUCTIVE-ELIMINATION; WACKER REACTION; BOND FORMATION; OXIDATION; WATER; DIOXYGENATION; DIBORON;

D O I：

10.1021/acs.orglett.8b01806

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel palladium-catalyzed alkene diacetoxylation with dioxygen (O-2) as both the sole oxidant and oxygen source is developed, which was identified by O-18-isotope labeling studies. Control experiments suggested that bis(pinacolato)diboron (B(2)pin(2)) played a dominant intermediary role in the formation of a C-O bond. This method performed good functional group tolerance with moderate to excellent yields, which could be successfully applied to the late-stage modification of natural products. Furthermore, an atmospheric pressure of dioxygen enhances the practicability of the protocol.

引用

收藏

页码：5090 / 5093

页数：4

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