Rhodium-Catalyzed Successive C-H Bond Functionalizations To Synthesize Complex Indenols Bearing a Benzofuran Unit

被引：13

作者：

Mei, Yan-Le ^{[1
]}

Zhou, Wei ^{[1
]}

Huo, Tao ^{[1
]}

Zhou, Fang-Shuai ^{[1
]}

Xue, Jing ^{[1
]}

Zhang, Guang-Yi ^{[1
]}

Ren, Bing-Tao ^{[1
]}

Zhong, Cheng ^{[2
]}

Deng, Qing-Hai ^{[1
]}

机构：

[1] Shanghai Normal Univ, Shanghai Key Lab Rare Earth Funct Mat, Joint Lab Int Cooperat Resource Chem, Educ Minist,Key Lab Resource Chem, Shanghai 200234, Peoples R China

[2] Wuhan Univ, Coll Chem & Mol Sci, 199 Bayi Rd, Wuhan 430072, Hubei, Peoples R China

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 23期

基金：

中国国家自然科学基金;

关键词：

N-PHENOXYACETAMIDES; DIRECTING GROUPS; PRIVILEGED SCAFFOLD; DRUG DISCOVERY; ACTIVATION; ALKYNES; ANNULATION; CARBOCYCLIZATION; DERIVATIVES; KETONES;

D O I：

10.1021/acs.orglett.9b03766

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient rhodium-catalyzed redox-neutral annulations of N-phenoxyacetamides and ynones via successive double C-H bond activations has been developed. A series of novel and complex indenols bearing a benzofuran unit were generated with moderate to excellent regioselecetivities under mild conditions. Adding N-ethylcyclohexanamine (CyNHEt) could restrict the formation of the mono C-H bond activation byproduct, which is not the intermediate of the reaction demonstrated via the mechanistic investigations.

引用

页码：9598 / 9602

页数：5

共 62 条

[1] Premithramycinone G, an early shunt product of the mithramycin biosynthetic pathway accumulated upon inactivation of oxygenase MtmOII
Abdelfattah, Mohamed S.
Rohr, Jurgen
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (34) : 5685 - 5689
[2] [Anonymous], 2016, CHEM DRUG DESIGN
[3] Anthraquinones as a privileged scaffold in drug discovery targeting nucleotide-binding proteins
Baqi, Younis
[J]. DRUG DISCOVERY TODAY, 2016, 21 (10) : 1571 - 1577
[4] Ruthenium(II)-Catalyzed Oxidative Double C-H Activation and Annulation Reaction: Synthesis of Indolo[2,1-a]isoquinolines
Borthakur, Somadrita
Sarma, Bipul
Gogoi, Sanjib
[J]. ORGANIC LETTERS, 2019, 21 (19) : 7878 - 7882
[5] Caruso A., 2019, MOLECULES, V24, P1912
[6] Hydroxyl Group-Prompted and Iridium(III)-Catalyzed Regioselective C-H Annulation of N-phenoxyacetamides with Propargyl Alcohols
Chen, Weijie
Liu, Fu-Xiaomin
Gong, Wanchun
Zhou, Zhi
Gao, Hui
Shi, Jingjing
Wu, Bo
Yi, Wei
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (13) : 2470 - 2475
[7] Transition metal-catalyzed C-H bond functionalizations by the use of diverse directing groups
Chen, Zhengkai
Wang, Binjie
Zhang, Jitan
Yu, Wenlong
Liu, Zhanxiang
Zhang, Yuhong
[J]. ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (09): : 1107 - 1295
[8] Ruthenium-Catalyzed Regioselective Cyclization of Aromatic Ketones with Alkynes: An Efficient Route to Indenols and Benzofulvenes
Chinnagolla, Ravi Kiran
Jeganmohan, Masilamani
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (02) : 417 - 423
[9] Beyond Friedel and Crafts: Directed Alkylation of C-H Bonds in Arenes
Evano, Gwilherm
Theunissen, Cedric
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (22) : 7202 - 7236
[10] Triphosgene and DMAP as Mild Reagents for Chemoselective Dehydration of Tertiary Alcohols
Ganiu, Moshood O.
Cleveland, Alexander H.
Paul, Jarrod L.
Kartika, Rendy
[J]. ORGANIC LETTERS, 2019, 21 (14) : 5611 - 5615

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