Vinylene Carbonate as Synthon in Transition Metal-Catalyzed C-H Bond Activation/Annulation Reactions

被引：14

作者：

Cui, Xiaofan ^{[1
,2
]}

Chauvin, Remi ^{[1
,2
,3
]}

Pi, Chao ^{[1
,2
]}

Wu, Yangjie ^{[1
,2
]}

Cui, Xiuling ^{[1
,2
]}

机构：

[1] Zhengzhou Univ, Green Catalysis Ctr, Key Lab Appl Chem Henan Univ, Henan Key Lab Chem Biol & Organ Chem, Zhengzhou 450052, Peoples R China

[2] Zhengzhou Univ, Coll Chem, Zhengzhou 450052, Peoples R China

[3] Univ Toulouse, LCC, Toulouse 3 Paul Sabatier, 205 Route Narbonne, F-31077 Toulouse, France

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2023年 / 365卷 / 20期

关键词：

C-H bond activation; Vinylene carbonate; Transition-metal-catalysis; Heterocycles; ANNULATION; AROMATICITY; CYCLIZATION;

D O I：

10.1002/adsc.202300601

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Recently, vinylene carbonate has been developed as a powerful synthon in transition metal-catalyzed C-H bond activation/cyclization reactions. This review introduces recent progress in the use of vinylene carbonate as a reactant, by analyzing and comparing reaction models involving vinylene carbonate as a surrogate of ethynol, acetylene, acetylation reagents or other reactants, while addressing related mechanisms and synthetic applications. image

引用

页码：3400 / 3412

页数：13

共 47 条

[1] Cross-Coupling of α-Carbonyl Sulfoxonium Ylides with C-H Bonds [J].

Barday, Manuel ;

Janot, Christopher ;

Halcovitch, Nathan R. ;

Muir, James ;

Aissa, Christophe .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (42) :13117-13121

[2] Alkenylation of Arenes and Heteroarenes with Alkynes [J].

Boyarskiy, Vadim P. ;

Ryabukhin, Dmitry S. ;

Bokach, Nadezhda A. ;

Vasilyev, Aleksander V. .

CHEMICAL REVIEWS, 2016, 116 (10) :5894-5986

[3] Homologation Reaction of Ketones with Diazo Compounds [J].

Candeias, Nuno R. ;

Paterna, Roberta ;

Gois, Pedro M. P. .

CHEMICAL REVIEWS, 2016, 116 (05) :2937-2981

[4] Variation of aromaticity by twisting or expanding the ring content [J].

Chauvin, Remi ;

Lepetit, Christine ;

Maraval, Valerie ;

Leroyer, Leo .

PURE AND APPLIED CHEMISTRY, 2010, 82 (04) :769-800

[5] Carbo-Benzene's Aromaticity, Before and Beyond: A Tribute to Nozoe [J].

Cocq, Kevin ;

Maraval, Valerie ;

Saffon-Merceron, Nathalie ;

Chauvin, Remi .

CHEMICAL RECORD, 2015, 15 (01) :347-361

[6] Recent Advances in the Stereoselective Synthesis of Aziridines [J].

Degennaro, Leonardo ;

Trinchera, Piera ;

Luisi, Renzo .

CHEMICAL REVIEWS, 2014, 114 (16) :7881-7929

[7] Strategies for Innovation in Multicomponent Reaction Design [J].

Ganem, Bruce .

ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (03) :463-472

[8] Oxidative C-H/C-H Annulation of Imidazopyridines and Indazoles through Rhodium-Catalyzed Vinylene Transfer [J].

Ghosh, Koushik ;

Nishii, Yuji ;

Miura, Masahiro .

ORGANIC LETTERS, 2020, 22 (09) :3547-3550

[9] Rhodium-Catalyzed Annulative Coupling Using Vinylene Carbonate as an Oxidizing Acetylene Surrogate [J].

Ghosh, Koushik ;

Nishii, Yuji ;

Miura, Masahiro .

ACS CATALYSIS, 2019, 9 (12) :11455-11460

[10] Highly Enantioselective Cyclopropenation Reaction of 1-Alkynes with α-Alkyl-α-Diazoesters Catalyzed by Dirhodium(II) Carboxylates [J].

Goto, Takayuki ;

Takeda, Koji ;

Shimada, Naoyuki ;

Nambu, Hisanori ;

Anada, Masahiro ;

Shiro, Motoo ;

Ando, Kaori ;

Hashimoto, Shunichi .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (30) :6803-6808

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