Synthesis of Spirocyclohexadienones via Palladium-Catalyzed Dearomatization of Dibenzoxaborins

被引：3

作者：

Zhao, Yuyao ^{[1
]}

Sun, Lincong ^{[1
]}

Chang, Junbiao ^{[1
]}

Liu, Bingxian ^{[1
]}

机构：

[1] Henan Normal Univ, Sch Chem & Chem Engn, State Key Lab Antiviral Drugs, Pingyuan Lab, Xinxiang 453007, Henan, Peoples R China

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 05期

基金：

中国博士后科学基金; 国家重点研发计划;

关键词：

ASYMMETRIC DEAROMATIZATION; ALKYNES; SPIROANNULATION; ANNULATION; NAPHTHOLS; PHENOL; 2-ALKENYLPHENOLS; 2-ARYLPHENOLS; SPIROCYCLES; CYCLIZATION;

D O I：

10.1021/acs.orglett.3c04244

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The development of Pd-(II)-catalyzed dearomatization transformation of dibenzoxaborins with alkynes triggered by transmetalation from boron to palladium has been achieved, leading to the synthesis of spirocyclohexadienones, an important skeleton demonstrating potential biomedical utility. The [3 + 2] spiroannulation exhibits remarkable regioselectivity and broad substrate scope under mild reaction conditions. This methodology employs dibenzoxaborin as a substrate to establish the formal dearomatization of 2-phenylphenol, which poses a formidable energy barrier to the destruction of aromaticity.

引用

页码：1056 / 1061

页数：6

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