Synthesis of Fluorenes with an All-Carbon Quaternary Center via Palladium-Catalyzed Dual Arylation using Cyclic Diaryliodonium Triflates

被引：29

作者：

Peng, Xiaopeng ^{[1
,2
,3
,4
,7
]}

Luo, Hongwen ^{[1
,2
,3
,4
]}

Wu, Fuhai ^{[4
]}

Zhu, Daqian ^{[1
,2
,3
]}

Ganesan, A. ^{[6
]}

Huang, Peng ^{[1
,2
,3
,5
]}

Wen, Shijun ^{[1
,2
,3
,5
]}

机构：

[1] Sun Yat Sen Univ, Ctr Canc, 651 Dongfeng East Rd, Guangzhou 510060, Guangdong, Peoples R China

[2] Sun Yat Sen Univ, State Key Lab Oncol South China, 651 Dongfeng East Rd, Guangzhou 510060, Guangdong, Peoples R China

[3] Sun Yat Sen Univ, Collaborat Innovat Ctr Canc Med, 651 Dongfeng East Rd, Guangzhou 510060, Guangdong, Peoples R China

[4] Guangdong Pharmaceut Univ, 280 Waihuan East Rd, Guangzhou 510006, Guangdong, Peoples R China

[5] Sun Yat Sen Univ, Sch Pharmaceut Sci, 132 Waihuan East Rd, Guangzhou 510006, Guangdong, Peoples R China

[6] Univ East Anglia, Sch Pharm, Norwich NR4 7TJ, Norfolk, England

[7] Zhaoqing Med Coll, 6 West River Rd, Zhaoqing 526060, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2017年 / 359卷 / 07期

基金：

中国国家自然科学基金;

关键词：

arylation; diaryliodonium triflates; fluorenes; palladium; quaternary center; BUTOXIDE-MEDIATED ARYLATION; C-H; SALTS; ALKYNES; ARYL; DERIVATIVES; TRANSFORMATION; PRODUCTS; BROMIDES; KETONES;

D O I：

10.1002/adsc.201601260

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Catalyzed by palladium species, cyclic diaryliodonium salts underwent dual C-aryl functionalization smoothly with activated methylene sources. With this new finding, a series of diversified fluorenes with an all-carbon quaternary center was quickly constructed. Moreover, our approach also provided various novel spirofluorenes containing barburate acid or indane motifs which are featured in medicinal drugs and functional materials.

引用

页码：1152 / 1156

页数：5

共 52 条

[1]

[Anonymous], 2012, ANGEW CHEM

[2]

Barluenga J., 2006, ANGEW CHEM, V118, P3212

[3] Direct intramolecular arylation of aldehydes promoted by reaction with IPy2BF4/HBF4:: Synthesis of benzocyclic ketones [J].

Barluenga, Jose ;

Trincado, Monica ;

Rubio, Eduardo ;

Gonzalez, Jose M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (19) :3140-3143

[4] Arylation of Azlactones using Diaryliodonium Bromides and Silver Carbonate: Facile Access to α-Tetrasubstituted Amino Acid Derivatives [J].

Chai, Zhuo ;

Wang, Biao ;

Chen, Jia-Nan ;

Yang, Gaosheng .

ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (11-12) :2714-2718

[5]

Chidipudi S. Reddy, 2012, ANGEW CHEM, V124, P12281

[6] Functionalization of Csp3-H and Csp2-H Bonds: Synthesis of Spiroindenes by Enolate-Directed Ruthenium-Catalyzed Oxidative Annulation of Alkynes with 2-Aryl-1,3-dicarbonyl Compounds [J].

Chidipudi, Suresh Reddy ;

Khan, Imtiaz ;

Lam, Hon Wai .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (48) :12115-12119

[7] Palladium-catalyzed α-arylation of carbonyl compounds and nitriles [J].

Culkin, DA ;

Hartwig, JF .

ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (04) :234-245

[8]

Du Y., 2016, ANGEW CHEM, V128, P1769, DOI [10.1002/ange.201509014, DOI 10.1002/ANGE.201509014, DOI 10.1002/ANIE.201509014]

[9] Ionic Covalent Organic Frameworks with Spiroborate Linkage [J].

Du, Ya ;

Yang, Haishen ;

Whiteley, Justin Michael ;

Wan, Shun ;

Jin, Yinghua ;

Lee, Se-Hee ;

Zhang, Wei .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (05) :1737-1741

[10] REARRANGEMENT ORGANOMETALLIC COMPOUNDS .25. CARBON-SKELETAL [1,2] ANIONIC REARRANGEMENTS AND THE PI-ORBITAL OVERLAP CONSTRAINT - THE QUESTION OF NUCLEOPHILIC-ATTACK VERSUS ELECTRON-TRANSFER [J].

EISCH, JJ ;

KOVACS, CA ;

CHOBE, P .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (06) :1275-1284

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