Synthesis of Indole/Benzofuran-Containing Diarylmethanes through Palladium-Catalyzed Reaction of Indolylmethyl or Benzofuranylmethyl Acetates with Boronic Acids

被引：7

作者：

Arcadi, Antonio ^{[1
,2
]}

Calcaterra, Andrea ^{[3
]}

Chiarini, Marco ^{[4
]}

Fabrizi, Giancarlo ^{[3
]}

Fochetti, Andrea ^{[3
]}

Goggiamani, Antonella ^{[3
]}

Iazzetti, Antonia ^{[5
]}

Marrone, Federico ^{[3
]}

Marsicano, Vincenzo ^{[2
]}

Serraiocco, Andrea ^{[3
]}

机构：

[1] Univ Aquila, Dipartimento Ingn & Sci Informaz & Matemat, Via Vetoio, I-67100 Coppito, AQ, Italy

[2] Univ Aquila, Dipartimento Sci Fis & Chim, I-67100 Coppito, AQ, Italy

[3] Sapienza Univ Roma, Dipartimento Chim & Tecnol Farmaco, Ple A Moro 5, I-00185 Rome, Italy

[4] Univ Teramo, Fac Biosci & Tecnol Agroalimentari & Ambientali, Via R Balzarini 1, I-64100 Teramo, Italy

[5] Univ Cattolica Sacro Cuore, Clin Intensivol & Perioperatorie, Dipartimento Sci Biotecnol Base, Lgo Francesco Vito 1, I-00168 Rome, Italy

来源：

SYNTHESIS-STUTTGART | 2022年 / 54卷 / 03期

关键词：

palladium; boronic acids; Suzuki-Miyaura reaction; indoles; benzofurans; diarylmethanes; NUCLEOPHILIC-SUBSTITUTION; BENZYLIC SUBSTITUTION; NITROGEN-HETEROCYCLES; INDOLE; DERIVATIVES; BENZYLATION; CARBONATES; COMPLEXES; SCAFFOLD; OPTIMIZATION;

D O I：

10.1055/s-0041-1737275

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The palladium-catalyzed synthesis of indole/benzofuran-containing diarylmethanes starting from indolylmethyl or benzofuranylmethyl acetates with boronic acids has been investigated. The success of the reaction is influenced by the choice of precatalyst: with indolylmethyl acetates the reaction works well with [Pd(eta (3) -C (3) H (5) )Cl] (2) /XPhos while with benzofuranylmethyl acetates Pd (2) (dba) (3) /XPhos is more efficient. The good to high yields and the simplicity of the experimental procedure make this protocol a versatile synthetic tool for the preparation of 2- and 3-substituted indoles and 2-benzo[ b ]furans. The methodology can be advantageously extended to the preparation of a key precursor of Zafirlukast.

引用

页码：741 / 753

页数：13

共 74 条

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