Palladium-catalyzed synthesis of 2,3-disubstituted indoles via arylation of ortho-alkynylanilines with arylsiloxanes

被引：0

作者：

Hsia, Yang-Ting ^{[1
]}

Lu, Yu-Lin ^{[1
]}

Bai, Rekha ^{[1
]}

Badsara, Satpal Singh ^{[4
]}

Lee, Chin-Fa ^{[1
,2
,3
]}

机构：

[1] Natl Chung Hsing Univ, Dept Chem, Taichung 402, Taiwan

[2] Natl Chung Hsing Univ, I Ctr Adv Sci & Technol, Taichung 402, Taiwan

[3] Natl Chung Hsing Univ, Innovat & Dev Ctr Sustainable Agr, Taichung 402, Taiwan

[4] Univ Rajasthan, Dept Chem, MFOS Lab, Jaipur 302004, Rajasthan, India

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2023年 / 21卷 / 37期

关键词：

CROSS-COUPLING REACTIONS; SOLID-PHASE; O-ALKYNYLTRIFLUOROACETANILIDES; UNSYMMETRICAL BIARYLS; ARYL CHLORIDES; SILOXANE; FUNCTIONALIZATION; ALKYNES; DERIVATIVES; CYCLIZATION;

D O I：

10.1039/d3ob00961k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this study, we report the electrophilic cyclization of N,N-dimethyl-o-alkynylanilines with arylsiloxanes in the presence of [Pd(OAc)(2)] and Ag2O catalytic system, which leads to the efficient synthesis of indoles, similar to the one that is obtained through Larock indole synthesis. A range of aryl(trimethoxy)silanes with EDGs and EWGs were successfully utilized for the synthesis of a diverse variety of substituted indoles via the cleavage of the C-Si bond. This protocol exhibits good functional group tolerance and wide substrate scope to provide 2,3-diaryl-N-methylindoles in 26-88% yields.

引用

页码：7602 / 7610

页数：9

共 77 条

[1] Catalytic arylations with challenging substrates: From air-stable HASPO preligands to indole syntheses and C-H-bond functionalizations
Ackermann, Lutz
[J]. SYNLETT, 2007, (04) : 507 - 526
[2] Palladium-catalyzed reaction of o-alkynyltrifluoroacetanilides with 1-bromoalkynes.: An approach to 2-substituted 3-alkynylindoles and 2-substituted 3-acylindoles
Arcadi, A
Cacchi, S
Fabrizi, G
Marinelli, F
Parisi, LM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (16) : 6213 - 6217
[3] Battistuzzi G, 2002, EUR J ORG CHEM, V2002, P2671
[4] The Suzuki-Miyaura reaction after the Nobel prize
Beletskaya, Irina P.
Alonso, Francisco
Tyurin, Vladimir
[J]. COORDINATION CHEMISTRY REVIEWS, 2019, 385 : 137 - 173
[5] Arbidol:: A broad-spectrum antiviral compound that blocks viral fusion
Boriskin, Y. S.
Leneva, I. A.
Pecheur, E. -I.
Polyak, S. J.
[J]. CURRENT MEDICINAL CHEMISTRY, 2008, 15 (10) : 997 - 1005
[6] Synthesis and functionalization of Indoles through palladium-catalyzed reactions
Cacchi, S
Fabrizi, G
[J]. CHEMICAL REVIEWS, 2005, 105 (07) : 2873 - 2920
[7] Update 1 of: Synthesis and Functionalization of Indoles Through Palladium-Catalyzed Reactions
Cacchi, Sandro
Fabrizi, Giancarlo
[J]. CHEMICAL REVIEWS, 2011, 111 : PR215 - PR283
[8] Synthesis of 2-Substituted Benzothio(seleno)phenes and Indoles via Ag-Catalyzed Cyclization/Demethylation of 2-Alkynylthio(seleno)anisoles and 2-Alkynyldimethylanilines
Cai, Tao
Feng, Chengjie
Shen, Fangqi
Bian, Kejun
Wu, Chunlei
Shen, Runpu
Gao, Yuzhen
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (04) : 653 - 656
[9] Indoles as therapeutics of interest in medicinal chemistry: Bird's eye view
Chadha, Navriti
Silakari, Om
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2017, 134 : 159 - 184
[10] A facile synthesis of various fluorine-containing indole derivatives via palladium-catalyzed annulation of internal alkynes
Chae, J
Konno, T
Ishihara, T
Yamanaka, H
[J]. CHEMISTRY LETTERS, 2004, 33 (03) : 314 - 315

← 1 2 3 4 5 6 7 8 →