Regioselective C3Alkylation of Indoles for the Synthesis of Bis(indolyl)methanes and 3-Styryl Indoles

被引：27

作者：

Zhang, Ruiqin ^{[1
,2
,3
]}

Ma, Renchao ^{[1
,2
]}

Chen, Rener ^{[1
,2
]}

Wang, Lei ^{[1
,2
,4
]}

Ma, Yongmin ^{[1
,2
]}

机构：

[1] Taizhou Univ, Inst Adv Studies, Jiaojiang 318000, Peoples R China

[2] Taizhou Univ, Sch Pharmaceut Sci, Jiaojiang 318000, Peoples R China

[3] Zhejiang Chinese Med Univ, Sch Pharmaceut Sci, Hangzhou 310053, Peoples R China

[4] Hangzhou Normal Univ, Coll Mat Chem & Chem Engn, Minist Educ, Key Lab Organosilicon Chem & Mat Technol, Hangzhou 311121, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 03期

关键词：

PALLADIUM-CATALYZED DIRECT; FRIEDEL-CRAFTS ALKYLATION; C-H FUNCTIONALIZATION; BOND ACTIVATION; TRANSITION; ARYLATION; ALKENYLATION; DERIVATIVES; CONSTRUCTION; EFFICIENT;

D O I：

10.1021/acs.joc.3c02551

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we describe an efficient transition-metal-free regioselective C(3)alkylation of indoles for the synthesis of bis-(indolyl)-methanes and 3-styryl indoles. Nitrobenzene is employed as the oxidant to oxidize the alcohols in the presence of a strong base and the reaction avoids the use of transition metals such as Ru and Mn. The protocol provides a favorable route to access biologically active compounds such as arundine, vibrindole A, and turbomycin B.

引用

页码：1846 / 1857

页数：12

共 93 条

[1] One-Pot Construction of 3,3′-Bisindolylmethanes through Bartoli Indole Synthesis [J].

Abe, Takumi ;

Nakamura, Shuuhei ;

Yanada, Reiko ;

Choshi, Tominari ;

Hibino, Satoshi ;

Ishikura, Minoru .

ORGANIC LETTERS, 2013, 15 (14) :3622-3625

[2] B(3,4,5-F3H2C6)3 Lewis acid-catalysed C3-allylation of indoles [J].

Alotaibi, Nusaybah ;

Babaahmadi, Rasool ;

Pramanik, Milan ;

Kaehler, Tanja ;

Dasgupta, Ayan ;

Richards, Emma ;

Ariafard, Alireza ;

Wirth, Thomas ;

Melen, Rebecca L. L. .

DALTON TRANSACTIONS, 2023, 52 (16) :5039-5043

[3] B2(OH)4-Mediated Reductive Transamidation of N-Acyl Benzotriazoles with Nitro Compounds En Route to Aqueous Amide Synthesis [J].

Bai, Jin ;

Li, Shangzhang ;

Zhu, Riqian ;

Li, Yang ;

Li, Wanfang .

JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (06) :3714-3723

[4] B(C6F5)3-Catalyzed Direct C3 Alkylation of Indoles and Oxindoles [J].

Basak, Shyam ;

Alvarez-Montoya, Ana ;

Winfrey, Laura ;

Melen, Rebecca L. ;

Morrill, Louis C. ;

Pulis, Alexander P. .

ACS CATALYSIS, 2020, 10 (08) :4835-4840

[5] Direct palladium-catalyzed C-3 arylation of free (NH)-indoles with aryl bromides under ligandless conditions [J].

Bellina, Fabio ;

Benelli, Francesca ;

Rossi, Renzo .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (14) :5529-5535

[6] Chiral Phosphoric Acid Catalyzed Highly Enantioselective Friedel-Crafts Alkylation Reaction of C3-Substituted Indoles to β,γ-Unsaturated α-Ketimino Esters [J].

Bi, Bo ;

Lou, Qin-Xin ;

Ding, Yu-Yang ;

Chen, Sheng-Wei ;

Zhang, Sha-Sha ;

Hu, Wen-Hui ;

Zhao, Jun-Ling .

ORGANIC LETTERS, 2015, 17 (03) :540-543

[7] Ruthenium Pincer Complex Catalyzed Selective Synthesis of C-3 Alkylated Indoles and Bisindolylmethanes Directly from Indoles and Alcohols [J].

Biswas, Nandita ;

Sharma, Rahul ;

Srimani, Dipankar .

ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (14) :2902-2910

[8]

Bronner SM, 2011, HETEROCYCLES IN NATURAL PRODUCT SYNTHESIS, P221

[9] Cobalt-catalysed reductive C-H alkylation of indoles using carboxylic acids and molecular hydrogen [J].

Cabrero-Antonino, Jose R. ;

Adam, Rosa ;

Junge, Kathrin ;

Beller, Matthias .

CHEMICAL SCIENCE, 2017, 8 (09) :6439-6450

[10] Palladium-Catalyzed C-N Cross-Coupling of NH-Heteroarenes and Quaternary Ammonium Salts via C-N Bond Cleavage [J].

Chen, Hongyi ;

Yang, Hongqin ;

Li, Nutao ;

Xue, Xinghua ;

He, Ze ;

Zeng, Qingle .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2019, 23 (08) :1679-1685

← 1 2 3 4 5 6 7 8 9 10 →