C4-arylation and domino C4-arylation/3,2-carbonyl migration of indoles by tuning Pd catalytic modes: Pd(i)-Pd(ii) catalysis vs. Pd(ii) catalysis

被引：56

作者：

Cheng, Yaohang ^{[1
]}

Yu, Shijie ^{[1
]}

He, Yuhang ^{[1
]}

An, Guanghui ^{[1
]}

Li, Guangming ^{[1
]}

Yang, Zhenyu ^{[2
]}

机构：

[1] Heilongjiang Univ, Key Lab Funct Inorgan Mat Chem MOE, Sch Chem & Mat Sci, 74 Xuefu Rd, Harbin 150080, Heilongjiang, Peoples R China

[2] Taizhou Univ, Sch Pharmaceut & Mat Engn, 1139 Shifu Ave, Taizhou 318000, Peoples R China

来源：

CHEMICAL SCIENCE | 2021年 / 12卷 / 09期

关键词：

C-H ARYLATION; UNACTIVATED ALKYL-HALIDES; SITE-SELECTIVE ARYLATION; CROSS-COUPLING REACTIONS; HECK-TYPE REACTION; FLUOROALKYLATED ALKENES; FUNCTIONALIZATION; ACTIVATION; ARYL; OLEFINATION;

D O I：

10.1039/d0sc05409g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Efficient C4-arylation and domino C4-arylation/3,2-carbonyl migration of indoles have been developed. The former route enables C4-arylation in a highly efficient and mild manner and the latter route provides an alternative straightforward protocol for synthesis of C2/C4 disubstituted indoles. The mechanism studies imply that the different reaction pathways were tuned by the distinct acid additives, which led to either the Pd(i)-Pd(ii) pathway or Pd(ii) catalysis.

引用

页码：3216 / 3225

页数：10

共 114 条

[1] Designing Pd and Ni Catalysts for Cross-Coupling Reactions by Minimizing Off-Cycle Species [J].

Balcells, David ;

Nova, Ainara .

ACS CATALYSIS, 2018, 8 (04) :3499-3515

[2] Cobalt-Catalyzed Regioselective Direct C-4 Alkenylation of 3-Acetylindole with Michael Acceptors Using a Weakly Coordinating Functional Group [J].

Banjare, Shyam Kumar ;

Nanda, Tanmayee ;

Ravikumar, P. C. .

ORGANIC LETTERS, 2019, 21 (19) :8138-8143

[3] Palladium-Catalyzed Enantioselective Narasaka-Heck Reaction/Direct C-H Alkylation of Arenes: Iminoarylation of Alkenes [J].

Bao, Xu ;

Wang, Qian ;

Zhu, Jieping .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (32) :9577-9581

[4] Applications of Bartoli indole synthesis [J].

Bartoli, Giuseppe ;

Dalpozzo, Renato ;

Nardi, Monica .

CHEMICAL SOCIETY REVIEWS, 2014, 43 (13) :4728-4750

[5] Mild C-H Halogenation of Anilides and the Isolation of an Unusual Palladium(I)-Palladium(II) Species [J].

Bedford, Robin B. ;

Haddow, Mairi F. ;

Mitchell, Charlotte J. ;

Webster, Ruth L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (24) :5524-5527

[6] Rh(iii)-Catalyzed tandem indole C4-arylamination/annulation with anthranils: access to indoloquinolines and their application in photophysical studies [J].

Biswas, Aniruddha ;

Bera, Satabdi ;

Poddar, Puja ;

Dhara, Dibakar ;

Samanta, Rajarshi .

CHEMICAL COMMUNICATIONS, 2020, 56 (09) :1440-1443

[7]

Bonney KJ, 2014, CHEM SOC REV, V43, P6609, DOI [10.1039/C4CS00061G, 10.1039/c4cs00061g]

[8] Dinuclear Pd(I) complexes-solely precatalysts? Demonstration of direct reactivity of a Pd(I) dimer with an aryl iodide [J].

Bonney, Karl J. ;

Proutiere, Fabien ;

Schoenebeck, Franziska .

CHEMICAL SCIENCE, 2013, 4 (12) :4434-4439

[9] Rhodium-Catalyzed, Remote Terminal Hydroarylation of Activated Olefins through a Long-Range Deconjugative Isomerization [J].

Borah, Arun Jyoti ;

Shi, Zhuangzhi .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (19) :6062-6066

[10] Palladium-catalyzed regioselective C-H fluoroalkylation of indoles at the C4-position [J].

Borah, Arun Jyoti ;

Shi, Zhuangzhi .

CHEMICAL COMMUNICATIONS, 2017, 53 (28) :3945-3948

← 1 2 3 4 5 6 7 8 9 10 →