Imine induced metal-free C-H arylation of indoles

被引：11

作者：

Zhang, Lin ^{[1
]}

Gao, Jianan ^{[1
]}

Wang, Bin ^{[1
]}

Iqbal, Azhar ^{[3
]}

Jin, Weiwei ^{[1
]}

Xia, Yu ^{[1
]}

Zhang, Yonghong ^{[1
]}

Liu, Chenjiang ^{[1
,2
]}

机构：

[1] Xinjiang Univ, Urumqi Key Lab Green Catalysis & Synth Technol, Coll Chem,State Key Lab Chem & Utilizat Carbon Ba, Key Lab Oil & Gas Fine Chem,Minist Educ & Xinjian, Urumqi 830017, Peoples R China

[2] Xinjiang Univ, Coll Future Technol, Urumqi 830017, Peoples R China

[3] Bacha Khan Univ, Dept Chem, Charsadda, Pakistan

来源：

ORGANIC CHEMISTRY FRONTIERS | 2023年 / 10卷 / 24期

关键词：

DIRECTING GROUP; ARYLTRIAZENES; ALKENES; KETONE;

D O I：

10.1039/d3qo01002c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report a metal-free and mild protocol for the direct arylation of indole at the C2 position using an imine transient directing group. Aryltriazenes are used as the aryl source with controllable activity, releasing the aryl radical and amine in a sustained manner under the action of a promoter. The transient imine directing groups were generated in situ by condensation of indole-3-carbaldehydes and the released amine to facilitate the direct C2 arylation of indoles via aryl radical addition with the assistance of transient unsaturated imine. This strategy is characterized by the absence of additional auxiliary groups, simple operation, and metal-free and mild reaction conditions, and provides insight into the metal-free direct arylation of indoles induced by in situ generated transient directing groups. A simple, mild, and metal- and extra-auxiliary group-free method for the direct arylation of indole-3-carbaldehydes induced by an in situ generated transient directing group was developed.

引用

页码：6063 / 6069

页数：8

共 54 条

[1] New strategies for organic catalysis: The first highly enantioselective organocatalytic Diels-Alder reaction [J].

Ahrendt, KA ;

Borths, CJ ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) :4243-4244

[2] Antitumor activity of bis-indole derivatives [J].

Andreani, Aldo ;

Burnelli, Silvia ;

Granaiola, Massimiliano ;

Leoni, Alberto ;

Locatelli, Alessandra ;

Morigi, Rita ;

Rambaldi, Mirella ;

Varoli, Lucilla ;

Landi, Laura ;

Prata, Cecilia ;

Berridge, Michael V. ;

Grasso, Carole ;

Fiebig, Heinz-Herbert ;

Kelter, Gerhard ;

Burger, Angelika M. ;

Kunkel, Mark W. .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (15) :4563-4570

[3] Mapping reactivities of aromatic models with a lignin disassembly catalyst. Steps toward controlling product selectivity [J].

Bernt, Christopher M. ;

Bottari, Giovanni ;

Barrett, Jacob A. ;

Scott, Susannah L. ;

Barta, Katalin ;

Ford, Peter C. .

CATALYSIS SCIENCE & TECHNOLOGY, 2016, 6 (09) :2984-2994

[4] Ionic Liquid Promoted Diazenylation of N-Heterocyclic Compounds with Aryltriazenes under Mild Conditions [J].

Cao, Dawei ;

Zhang, Yonghong ;

Liu, Chenjiang ;

Wang, Bin ;

Sun, Yadong ;

Abdukadera, Ablimit ;

Hu, Haiyan ;

Liu, Qiang .

ORGANIC LETTERS, 2016, 18 (09) :2000-2003

[5]

Chen J., 2020, Adv, V10

[6] C2/C4 Regioselective Heteroarylation of Indoles by Tuning C-H Metalation Modes [J].

Chen, Shuyou ;

Zhang, Min ;

Su, Rongchuan ;

Chen, Xingyu ;

Feng, Boya ;

Yang, Yudong ;

You, Jingsong .

ACS CATALYSIS, 2019, 9 (07) :6372-6379

[7] The Antinociceptive and Anti-Inflammatory Activities of Caulerpin, a Bisindole Alkaloid Isolated from Seaweeds of the Genus Caulerpa [J].

de Souza, Everton Tenorio ;

de Lira, Daysianne Pereira ;

de Queiroz, Aline Cavalcanti ;

Costa da Silva, Diogo Jose ;

de Aquino, Anansa Bezerra ;

Campessato Mella, Eliane A. ;

Lorenzo, Vitor Prates ;

de Miranda, George Emmanuel C. ;

de Araujo-Junior, Joao Xavier ;

de Oliveira Chaves, Maria Celia ;

Barbosa-Filho, Jose Maria ;

de Athayde-Filho, Petronio Filgueiras ;

de Oliveira Santos, Barbara Viviana ;

Alexandre-Moreira, Magna Suzana .

MARINE DRUGS, 2009, 7 (04) :689-704

[8] Microcalorimetric adsorption and infrared spectroscopic studies of supported nickel catalysts for the hydrogenation of diisopropylimine to diisopropylamine [J].

Deng, Lidan ;

Zhu, Jianxin ;

Chen, Hui ;

Wang, Hui ;

Shen, Jianyi .

JOURNAL OF CATALYSIS, 2018, 362 :35-45

[9] Enantioselective Pallada-Electrocatalyzed C-H Activation by Transient Directing Groups: Expedient Access to Helicenes [J].

Dhawa, Uttam ;

Tian, Cong ;

Wdowik, Tomasz ;

Oliveira, Joao C. A. ;

Hao, Jiping ;

Ackermann, Lutz .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (32) :13451-13457

[10] Emergence of Pyrimidine-Based meta-Directing Group: Journey from Weak to Strong Coordination in Diversifying meta-C-H Functionalization [J].

Dutta, Uttam ;

Maiti, Debabrata .

ACCOUNTS OF CHEMICAL RESEARCH, 2022, 55 (03) :354-372

← 1 2 3 4 5 6 →