Propargyl Alcohols as One-Carbon Synthons: Redox-Neutral Rhodium(III)-Catalyzed C-H Bond Activation for the Synthesis of Isoindolinones Bearing a Quaternary Carbon

被引：110

作者：

Wu, Xiaowei ^{[1
,2
]}

Wang, Bao ^{[1
,3
]}

Zhou, Yu ^{[1
]}

Liu, Hong ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Mat Med, Key Lab Receptor Res, 555 Chong Zhi Rd, Shanghai 201203, Peoples R China

[2] Univ Chinese Acad Sci, 19A Yuquan Rd, Beijing 100049, Peoples R China

[3] ShanghaiTech Univ, Sch Life Sci & Technol, 100 Haike Rd, Shanghai 201210, Peoples R China

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 06期

基金：

中国国家自然科学基金;

关键词：

FORM GAMMA-LACTAMS; O BOND; ISOQUINOLONE SYNTHESIS; EFFICIENT SYNTHESIS; INTERNAL OXIDANT; INDOLE SYNTHESIS; FACILE SYNTHESIS; DIRECTING GROUP; 4+1 ANNULATION; N-OXIDES;

D O I：

10.1021/acs.orglett.7b00089

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, rhodium(III)-catalyzed C-H activation/subsequent [4 + 1] cyclization reactions between benzamides and propargyl alcohols are reported in which propargyl alcohols serve as unusual one carbon units. This title transformation led to a series of isoindolinones bearing a quaternary carbon with moderate to good yields without the requirement for external metal oxidants. Due to the mild and simple reaction conditions, this reaction is compatible with various functional groups.

引用

页码：1294 / 1297

页数：4

共 56 条

[1] Ruthenium-Catalyzed C-H/N-O Bond Functionalization: Green Isoquinolone Syntheses in Water [J].

Ackermann, Lutz ;

Fenner, Sabine .

ORGANIC LETTERS, 2011, 13 (24) :6548-6551

[2] Smooth Isoindolinone Formation from Isopropyl Carbamates via Bischler-Napieralski-Type Cyclization [J].

Adachi, Satoshi ;

Onozuka, Masao ;

Yoshida, Yuko ;

Ide, Mitsuaki ;

Saikawa, Yoko ;

Nakata, Masaya .

ORGANIC LETTERS, 2014, 16 (02) :358-361

[3] Rhodium-Catalyzed (5+1) Annulations Between 2-Alkenylphenols and Allenes: A Practical Entry to 2,2-Disubstituted 2H-Chromenes [J].

Casanova, Noelia ;

Seoane, Andres ;

Mascarenas, Jose L. ;

Gulias, Moises .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (08) :2374-2377

[4] Formal [4+1] Annulation Reactions in the Synthesis of Carbocyclic and Heterocyclic Systems [J].

Chen, Jia-Rong ;

Hu, Xiao-Qiang ;

Lu, Liang-Qiu ;

Xiao, Wen-Jing .

CHEMICAL REVIEWS, 2015, 115 (11) :5301-5365

[5] Asymmetric synthesis of 3-substituted isoindolinones: Application to the total synthesis of (+)-lennoxamine [J].

Comins, DL ;

Schilling, S ;

Zhang, YC .

ORGANIC LETTERS, 2005, 7 (01) :95-98

[6] Multi-component syntheses of heterocycles by transition-metal catalysis [J].

D'Souza, Daniel M. ;

Mueller, Thomas J. J. .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) :1095-1108

[7] Selective Cyclization of Arylnitrones to Indolines under External Oxidant-Free Conditions: Dual Role of Rh(III) Catalyst in the C-H Activation and Oxygen Atom Transfer [J].

Dateer, Ramesh B. ;

Chang, Sukbok .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (15) :4908-4911

[8] A General Catalytic Route to Isoindolinones and Tetrahydroisoquinolines: Application in the Synthesis of (±)-Crispine A [J].

Dhanasekaran, Sivasankaran ;

Bisai, Vishnumaya ;

Unhale, Rajshekhar A. ;

Suneja, Arun ;

Singh, Vinod K. .

ORGANIC LETTERS, 2014, 16 (23) :6068-6071

[9] Tunable Arylative Cyclization of 1,6-Enynes Triggered by Rhodium(III)-Catalyzed C-H Activation [J].

Fukui, Yuki ;

Liu, Ping ;

Liu, Qiang ;

He, Zhi-Tao ;

Wu, Nuo-Yi ;

Tian, Ping ;

Lin, Guo-Qiang .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (44) :15607-15614

[10] Rhodium(III)-Catalyzed [4+1] Annulation of Aromatic and Vinylic Carboxylic Acids with Allenes: An Efficient Method Towards Vinyl-Substituted Phthalides and 2-Furanones [J].

Gandeepan, Parthasarathy ;

Rajamalli, Pachaiyappan ;

Cheng, Chien-Hong .

CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (25) :9198-9203

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