Highly Regioselective Synthesis of 2-Acylindolines through Cobalt-Catalyzed C-H Activation/[3+2] Annulation of Aniline Derivatives and Acrylates

被引：3

作者：

Tian, Xun ^{[1
]}

Pan, Ailin ^{[1
]}

Du, Ya ^{[1
]}

Zhang, Lening ^{[1
]}

Qin, Cuirong ^{[1
]}

Duan, Shengzu ^{[1
]}

Yang, Lijuan ^{[2
]}

Yang, Xiaodong ^{[1
]}

机构：

[1] Yunnan Univ, Yunnan Prov Ctr Res & Dev Nat Prod, Sch Pharm, Key Lab Med Chem Nat Resource,Minist Educ, Kunming 650500, Peoples R China

[2] Yunnan Minzu Univ, Sch Chem & Environm, Kunming 650500, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2022年 / 364卷 / 24期

基金：

国家重点研发计划;

关键词：

Highly regioselective; 2-Acylindolines; Cobalt-catalysis; C-H activation; 3+2] annulation; ACTIVATION/OXIDATIVE CYCLIZATION; INDOLINES; INDOLES; DIFUNCTIONALIZATION; TEMPERATURE; AMINATION; ACID;

D O I：

10.1002/adsc.202200965

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An approach for 2-acyl indolines synthesis through Cobalt-catalyzed C-H activation/[3+2] annulation of aniline derivatives and acrylates is described. The method employs cobalt catalyst to afford a wide variety of functionalized 2-acylindolines with high regioselectivity. The mechanism is investigated by KIE experiments and deuterium-labeling experiment. The gram-scale synthesis and synthetic transformations are also conducted, confirming the scalability and application value.

引用

页码：4421 / 4426

页数：6

共 50 条

[21] Palladium-catalyzed regioselective synthesis of 2(2′-biphenyl)benzimidazoles through C-H activation
Chen, Li-Hsun
Wu, Tz-Yi
Paike, Vijaykumar
Sun, Chung-Ming
MOLECULAR DIVERSITY, 2013, 17 (04) : 641 - 649
[22] Cobalt(II)-Catalyzed Directed C-H Functionalization/[3+2] Annulation of N-Arylguanidines with Alkynes
Parihar, Harish
Thirupathi, Natesan
ORGANIC LETTERS, 2022, : 8098 - 8103
[23] Rh(III)-Catalyzed [3+2] Annulation and C-H Alkenylation of Indoles with 1,3-Diynes by C-H Activation
Kumar, Sanjeev
Nunewar, Saiprasad
Usama, Khan Mohammad
Kanchupalli, Vinaykumar
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (15) : 2223 - 2229
[24] Rhodium-Catalyzed Enantioselective Oxidative [3+2] Annulation of Arenes and Azabicyclic Olefins through Twofold C-H Activation
Mi, Ruijie
Zheng, Guangfan
Qi, Zisong
Li, Xingwei
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (49) : 17666 - 17670
[25] Cobalt-catalyzed electrooxidative C-H/N-H [4+2] annulation with ethylene or ethyne
Shan Tang
Dan Wang
Yichang Liu
Li Zeng
Aiwen Lei
Nature Communications, 9
[26] Controlled Synthesis of Enantioselective 1-Aminoindenes via Cobalt-Catalyzed [3+2] Annulation Reaction
Chen, Min-Hsien
Hsieh, Jen-Chieh
Lee, Yi-Hsien
Cheng, Chien-Hong
ACS CATALYSIS, 2018, 8 (10): : 9364 - 9369
[27] Cobalt-Catalyzed Thioamide Directed C(arene)-H Annulation with Ynamide: Regioselective Access to 2-Amidoindenones
Sau, Somratan
Ghosh, Arghadip
Shankar, Majji
Gogoi, Manash Protim
Sahoo, Akhila Kumar
ORGANIC LETTERS, 2022, 24 (51) : 9508 - 9513
[28] Synthesis of Isoquinolinones via Regioselective Palladium-Catalyzed C-H Activation/Annulation
Qi, Wenke
Wu, Yimei
Han, Yongxu
Li, Yi
CATALYSTS, 2017, 7 (11)
[29] Cobalt-catalyzed electrooxidative C-H/N-H [4+2] annulation with ethylene or ethyne
Tang, Shan
Wang, Dan
Liu, Yichang
Zeng, Li
Lei, Aiwen
NATURE COMMUNICATIONS, 2018, 9
[30] Cobalt-catalyzed C-H activation/C-O formation: Synthesis of benzofuranones
Hajipour, Abdol R.
Khorsandi, Zahra
TETRAHEDRON LETTERS, 2020, 61 (03)

← 1 2 3 4 5 →