Cine-Substitutions at Five-Membered Hetarenes Enabled by Sulfonium Salts

被引：30

作者：

Berger, Florian ^{[1
]}

Alvarez, Eva Maria ^{[1
]}

Frank, Nils ^{[1
]}

Bohdan, Kostiantyn ^{[1
]}

Kondratiuk, Mykhailo ^{[1
]}

Torkowski, Luca ^{[1
]}

Engl, Pascal S. ^{[1
]}

Barletta, Joana ^{[1
]}

Ritter, Tobias ^{[1
]}

机构：

[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 14期

关键词：

C-H FUNCTIONALIZATION; HETEROARENES; ARYLATION; ACIDITIES;

D O I：

10.1021/acs.orglett.0c02067

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report a nucleophilic substitution reaction of five-membered hetarylsulfonium salts that results in a change of the substitution pattern on the arene. The products of these cine-substitutions are hard to access synthetically otherwise. The sulfonium salts that serve as starting materials are generated by a highly site-selective C-H functionalization reaction.

引用

页码：5671 / 5674

页数：4

共 34 条

[1] Pyrido-imidazodiazepinones as a new class of reversible inhibitors of human kallikrein 7 [J].

Arama, Dominique P. ;

Soualmia, Feryel ;

Lisowski, Vincent ;

Longevial, Jean-Francois ;

Bosc, Elodie ;

Maillard, Ludovic T. ;

Martinez, Jean ;

Masurier, Nicolas ;

El Amri, Chahrazade .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 93 :202-213

[2] Metal-free photoredox-catalysed formal C-H/C-H coupling of arenes enabled by interrupted Pummerer activation [J].

Aukland, Miles H. ;

Siauciulis, Mindaugas ;

West, Adam ;

Perry, Gregory J. P. ;

Procter, David J. .

NATURE CATALYSIS, 2020, 3 (02) :163-169

[3] Cine Substitution with Arylzinc Reagents: Scope and Mechanistic Studies [J].

Barroso, Santiago ;

Lemaire, Sebastien ;

Farina, Vittorio ;

Steib, Andreas K. ;

Blanc, Romain ;

Knochel, Paul .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (07) :2804-2816

[4] Site-selective and versatile aromatic C-H functionalization by thianthrenation [J].

Berger, Florian ;

Plutschack, Matthew B. ;

Riegger, Julian ;

Yu, Wanwan ;

Speicher, Samira ;

Ho, Matthew ;

Frank, Nils ;

Ritter, Tobias .

NATURE, 2019, 567 (7747) :223-228

[5] EQUILIBRIUM ACIDITIES IN DIMETHYL-SULFOXIDE SOLUTION [J].

BORDWELL, FG .

ACCOUNTS OF CHEMICAL RESEARCH, 1988, 21 (12) :456-463

[6] THE VONRICHTER REACTION .3. SUBSTITUENT EFFECTS [J].

BUNNETT, JF ;

RAUHUT, MM .

JOURNAL OF ORGANIC CHEMISTRY, 1956, 21 (09) :934-938

[7] STUDIES ON THE CONDITIONS, SCOPE AND MECHANISM OF THE VONRICHTER REACTION [J].

BUNNETT, JF ;

RAUHUT, MM ;

KNUTSON, D ;

BUSSELL, GE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (22) :5755-5761

[8] A complex catalytic cycle leading to a regioselective synthesis of o,o'-disubstituted vinylarenes [J].

Catellani, M ;

Frignani, F ;

Rangoni, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (1-2) :119-122

[9] Room-Temperature Direct β-Arylation of Thiophenes and Benzo[b]thiophenes and Kinetic Evidence for a Heck-type Pathway [J].

Colletto, Chiara ;

Islam, Saidul ;

Julia-Hernandez, Francisco ;

Larrosa, Igor .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (05) :1677-1683

[10] Pd/Norbornene: A Winning Combination for Selective Aromatic Functionalization via C-H Bond Activation [J].

Della Ca, Nicola ;

Fontana, Marco ;

Motti, Elena ;

Catellani, Marta .

ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (07) :1389-1400

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