Metallaphotoredox-catalyzed C-H activation: regio-selective annulation of allenes with benzamide

被引：15

作者：

Li, Tianlei ^{[1
,2
]}

Li, Jishun ^{[1
,2
,3
]}

Zhu, Zihao ^{[1
]}

Chen, Yuyuan ^{[1
]}

Li, Xueyao ^{[1
]}

Yang, Qingyun ^{[1
]}

Xia, Jie ^{[1
]}

Zhang, Wenxuan ^{[1
]}

Zhang, Chao ^{[4
,5
]}

Pan, Weidong ^{[2
,3
]}

Wu, Song ^{[1
]}

机构：

[1] Chinese Acad Med Sci & Peking Union Med Coll, Inst Mat Med, State Key Lab Bioact Substance & Funct Nat Med, Beijing 100005, Peoples R China

[2] Guizhou Med Univ, State Key Lab Funct & Applicat Med Plants, Guiyang 550014, Peoples R China

[3] Guizhou Univ Tradit Chinese Med Huaxi Univ Town, Guiyang 550025, Guizhou, Peoples R China

[4] Arizona State Univ, Biodesign Ctr BioEnerget, Tempe, AZ 85287 USA

[5] Arizona State Univ, Sch Mol Sci, Tempe, AZ 85287 USA

来源：

ORGANIC CHEMISTRY FRONTIERS | 2021年 / 8卷 / 05期

基金：

中国国家自然科学基金;

关键词：

VISIBLE-LIGHT PHOTOREDOX; FUNCTIONALLY-SUBSTITUTED ARYL; 1ST-ROW TRANSITION-METALS; INTERMOLECULAR ANNULATION; BOND FUNCTIONALIZATION; CYCLIZATION REACTIONS; ASYMMETRIC-SYNTHESIS; TERMINAL ALKYNES; COBALT; ALLYLATION;

D O I：

10.1039/d0qo01127d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have developed an efficient annulation of benzamides with allenes using cobalt and photoredox dual catalysis under an oxygen atmosphere. This reaction provides a mild and environmentally friendly method for the construction of isoquinolinone scaffolds in good to excellent yields, demonstrating broad substrate scopes, high regioselectivity, and good functional group compatibility. Notably, the transformation features an alternative strategy for the regeneration of a cobalt catalyst with the aid of Eosin Y. Preliminary mechanistic studies reveal that a radical-mediated cascade annulation is involved in this reaction.

引用

页码：928 / 935

页数：8

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