Synthesis of 2-(3-Arylallylidene)-3-oxindoles via Dirhodium(II)-Catalyzed Reaction of 3-Diazoindolin-2-imines with 1-Aryl-Substituted Allylic Alcohols and Computational Insights

被引：10

作者：

Gao, Ke ^{[1
]}

Kou, Luyao ^{[1
]}

Fu, Rui ^{[1
]}

Bao, Xiaoguang ^{[1
]}

机构：

[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Suzhou 215123, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2020年 / 362卷 / 06期

基金：

中国国家自然科学基金;

关键词：

Rhodium catalysis; alpha-Imino carbene; Oxindole; DFT calculation; INITIATED CLAISEN REARRANGEMENT; MEROCYANINE DYES; CATALYZED REACTION; TERMINAL ALKYNES; RHODIUM; FUNCTIONALIZATION; COPPER; INDOLES; CYCLOADDITION; ACCESS;

D O I：

10.1002/adsc.201901160

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A straightforward approach for the synthesis of 2-(3-arylallylidene)-3-oxindoles has been achieved by the dirhodium(II)-catalyzed reaction of 3-diazoindolin-2-imines with 1-aryl-substituted allylic alcohols. This protocol employs easily accessible feedstocks to produce oxindole derivatives, which might be applicable in the dye industry. DFT calculations were carried out to gain a mechanistic insight into the reaction.

引用

页码：1292 / 1297

页数：6

共 50 条

[1] Preparation of 3-Aryl-2-aminoindoles via Rhodium-Catalyzed Coupling Reaction between 2-Arylpyridines and 3-Diazoindolin-2-imines
Li, Zhenmin
Zhou, Xiaorong
Lu, Ping
Wang, Yanguang
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (19): : 9433 - 9437
[2] Co(III)-catalyzed reaction between 3-diazoindolin-2-imines and 1-pyrimidinylindoles for the synthesis of 2,3′-biindoles
Li, Zhenmin
Xie, Jianwei
Wu, Li
Suleman, Muhammad
Lu, Ping
Wang, Yanguang
TETRAHEDRON, 2020, 76 (31-32)
[3] Rh-Catalyzed Reactions of 3-Diazoindolin-2-imines: Synthesis of Pyridoindoles and Tetrahydrofuropyrroloindoles
Wang, Chen
Zhang, Haojie
Lang, Bo
Ren, Anni
Lu, Ping
Wang, Yanguang
ORGANIC LETTERS, 2015, 17 (18) : 4412 - 4415
[4] Palladium-Catalyzed Synthesis of 3-Haloindol-2-amines from 3-Diazoindolin-2-imines and Alkyl Halides
Zhou, Yuxuan
Li, Zhenmin
Ma, Fanghui
Zhao, Chang
Lu, Ping
Wang, Yanguang
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (11): : 6655 - 6668
[5] TfOH-Catalyzed Reaction between 3-Diazoindolin-2-imines and Electron-Rich Arenes: Access to 3-Aryl-2-aminoindoles
Qi, Jie
Wang, Zaibin
Lang, Bo
Lu, Ping
Wang, Yanguang
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (23): : 12640 - 12646
[6] Copper-catalyzed synthesis of 3-allyl-2-aminoindoles from 3-diazoindolin-2-imines and allyltrimethylsilane
Lang, Bo
Zhou, Yuxuan
Lu, Ping
Wang, Yanguang
TETRAHEDRON, 2019, 75 (12) : 1597 - 1604
[7] Preparation of 2-Amino-3-arylindoles via Pd-Catalyzed Coupling between 3-Diazoindolin-2-imines and Arylboronic Acids as well as Their Extension to 3-Aryl-3-fluoroindolin-2-imines
Ding, Hualong
Bai, Songlin
Lu, Ping
Wang, Yanguang
ORGANIC LETTERS, 2017, 19 (17) : 4604 - 4607
[8] Ru(ii)-catalyzed synthesis of indolo[2,3-c]isoquinolines via [3+3] annulation of N,N'-cyclic azomethine ylides and 3-diazoindolin-2-imines
Valapil, Durgesh Gurukkala
Mishra, Priyanka
Jungare, Kalyani
Shankaraiah, Nagula
NEW JOURNAL OF CHEMISTRY, 2023, 47 (37) : 17586 - 17591
[9] Rhodium-Catalyzed Cycloadditions between 3-Diazoindolin-2-imines and 1,3-Dienes
Lang, Bo
Zhu, Huangtianzhi
Wang, Chen
Lu, Ping
Wang, Yanguang
ORGANIC LETTERS, 2017, 19 (07) : 1630 - 1633
[10] A copper-catalyzed reaction of 3-diazoindolin-2-imines with 2-(phenylamino)ethanols: convenient access to spiro[indoline-3,2′-oxazolidin]-2-imines
Sheng, Guorong
Ma, Shicong
Bai, Songlin
Mao, Jianming
Lu, Ping
Wang, Yanguang
CHEMICAL COMMUNICATIONS, 2018, 54 (12) : 1529 - 1532

← 1 2 3 4 5 →