Radical reactions of aryl alkynoates in organic synthesis: Recent advances

被引：30

作者：

Ni, Shengyang ^{[1
]}

Zhou, Jie ^{[2
]}

Mei, Haibo ^{[1
]}

Han, Jianlin ^{[1
]}

机构：

[1] Nanjing Univ, Sch Chem & Chem Engn, State Key Lab Coordinat Chem, Nanjing 210093, Jiangsu, Peoples R China

[2] Nanjing Univ, Shenzhen Res Inst, Shenzhen 518057, Peoples R China

来源：

TETRAHEDRON LETTERS | 2018年 / 59卷 / 14期

基金：

中国国家自然科学基金;

关键词：

Aryl alkynoates; Cyclization; Migration; Difunctionalization; Decarboxylation; METAL-FREE CONDITIONS; FRIEDEL-CRAFTS ALKENYLATION; CROSS-COUPLING REACTIONS; C BOND FORMATIONS; ACTIVATED ALKYNES; OXIDATIVE DIFUNCTIONALIZATION; DEAROMATIVE SPIROCYCLIZATION; MEDICINAL CHEMISTRY; BIOLOGICAL-ACTIVITY; CASCADE REACTION;

D O I：

10.1016/j.tetlet.2018.02.055

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aryl alkynoate is an important intermediate and powerful synthetic tool in organic chemistry, because it contains acetylene bond which can be easily introduced of different functional groups. During the past decades, several types of reactions and coupling partners have been developed for the functionalization of aryl alkynoates. In this review, we summarize the recent advances on the reactions of aryl alkynoates, including direct cyclization, ester group migration/cyclization, aryl migration/decarboxylation, ipsocyclization/clearomatization, and other reactions in the past decade. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：1309 / 1316

页数：8

共 57 条

[31] Recycling the Waste: The Development of a Catalytic Wittig Reaction [J].

O'Brien, Christopher J. ;

Tellez, Jennifer L. ;

Nixon, Zachary S. ;

Kang, Lauren J. ;

Carter, Andra L. ;

Kunkel, Stephen R. ;

Przeworski, Katherine C. ;

Chass, Gregory A. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (37) :6836-6839

[32] Metal-Free Cascade Oxidative Decarbonylative Alkylation/Arylation of Alkynoates with Alphatic Aldehydes [J].

Pan, Changduo ;

Chen, Yu ;

Song, Shuai ;

Li, Lei ;

Yu, Jin-Tao .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (23) :12065-12069

[33] Metal-free radical addition/cyclization of alkynoates with xanthates towards 3-(β-carbonyl)coumarins [J].

Pan, Changduo ;

Chen, Rongzhen ;

Shao, Weile ;

Yu, Jin-Tao .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (38) :9033-9039

[34] Oxidative difunctionalization of alkynoates via cascade radical addition, aryl migration, and decarboxylation [J].

Pan, Changduo ;

Zhang, Honglin ;

Zhu, Chengjian .

TETRAHEDRON LETTERS, 2016, 57 (05) :595-598

[35] Tandem oxidative radical brominative addition of activated alkynes and spirocyclization: switchable synthesis of 3-bromocoumarins and 3-bromo spiro-[4,5] trienone [J].

Qiu, Guanyinsheng ;

Liu, Tong ;

Ding, Qiuping .

ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (04) :510-515

[36] Furocoumarins in medicinal chemistry. Synthesis, natural occurrence and biological activity [J].

Santana, L ;

Uriarte, E ;

Roleira, F ;

Milhazes, N ;

Borges, F .

CURRENT MEDICINAL CHEMISTRY, 2004, 11 (24) :3239-3261

[37] Efficient functionalization of aromatic C-H bonds catalyzed by gold(III) under mild and solvent-free conditions [J].

Shi, ZJ ;

He, C .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (11) :3669-3671

[38] Dramatic enhancement of catalytic activity in an ionic liquid: Highly practical Friedel-Crafts alkenylation of arenes with alkynes catalyzed by metal triflates [J].

Song, CE ;

Jung, DU ;

Choung, SY ;

Roh, EJ ;

Lee, SG .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (45) :6183-6185

[39] Copper-Catalyzed Electrophilic Carbofunctionalization of Alkynes to Highly Functionalized Tetrasubstituted Alkenes [J].

Suero, Marcos G. ;

Bayle, Elliott D. ;

Collins, Beatrice S. L. ;

Gaunt, Matthew J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (14) :5332-5335

[40] Electrophilic ipso-Cyclization of N-(p-Methoxyaryl)propiolamides Involving an Electrophile-Exchange Process [J].

Tang, Bo-Xiao ;

Yin, Qin ;

Tang, Ri-Yuan ;

Li, Jin-Heng .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (22) :9008-9011

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