Rhodium(III)-Catalyzed Direct C-H Alkylation of 2-Aryl-1,2,3-triazole N-Oxides with Maleimides

被引：12

作者：

Zhao, Juanli ^{[1
]}

Pi, Chao ^{[1
]}

You, Chang ^{[1
]}

Wang, Yong ^{[1
]}

Cui, Xiuling ^{[1
]}

Wu, Yangjie ^{[1
]}

机构：

[1] Zhengzhou Univ, Dept Chem, Henan Key Lab Chem Biol & Organ Chem, Key Lab Appl Chem Henan Univ, 75 Daxue St, Zhengzhou 450052, Henan, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 2018卷 / 48期

关键词：

Alkylation; High atom efficiency; Regioselectivity; Rhodium catalysis; UNACTIVATED C(SP(3))-H BONDS; CATALYZED DIRECT ALKYLATION; DIAZO-COMPOUNDS; CLICK CHEMISTRY; FUNCTIONALIZATION; CYCLIZATION; ACTIVATION; ARENES; DERIVATIVES; BENZAMIDES;

D O I：

10.1002/ejoc.201801353

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient rhodium(III)-catalyzed direct C-H ortho-alkylation of 2-aryl-1,2,3-triazole N-oxides has been developed using maleimides as the alkylation reagent. This protocol displays good functional group tolerance, high atom efficiency and avoids the external oxidant. Only mono-substituted products were obtained. Based on the results of deuterium exchange experiments, the N-oxide group plays an important role to improve the regioselectivity by increasing the steric hindrance.

引用

页码：6919 / 6923

页数：5

共 50 条

[31] Palladium-Catalyzed Aerobic Oxidative C-H Olefination with Removable 1,2,3-Triazole Directing Group
Ye, Xiaohan
Shi, Xiaodong
ORGANIC LETTERS, 2014, 16 (17) : 4448 - 4451
[32] Ruthenium-catalyzed 1,2,3-triazole directed intermolecular C-H amidation of arenes with sulfonyl azides
Wang, Xiaoyu
Zhang, Chen
Li, Jue
Jiang, Chong
Su, Fu
Zhan, Zhen
Hai, Li
Chen, Zhonghua
Wu, Yong
RSC ADVANCES, 2016, 6 (73) : 68929 - 68933
[33] Rhodium(III)-Catalyzed Oxidative C-H Alkylation of Aniline Derivatives with Allylic Alcohols To Produce β-Aryl Ketones
Khake, Shrikant M.
Chatani, Naoto
ACS CATALYSIS, 2022, 12 (08) : 4394 - 4401
[34] Rhodium(III)-catalyzed oxidative annulation of N-arylbenzamidines with maleimides via dual C-H activation
Sankaram, G. Siva
Sahoo, Tanmoy
Sridhar, B.
Reddy, B. V. Subba
ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (08) : 1719 - 1724
[35] Rhodium-Catalyzed C-H Alkylation of Indolines with Allylic Alcohols: Direct Access to β-Aryl Carbonyl Compounds
Han, Sang Hoon
Choi, Miji
Jeong, Taejoo
Sharma, Satyasheel
Mishra, Neeraj Kumar
Park, Jihye
Oh, Joa Sub
Kim, Woo Jung
Lee, Jong Suk
Kim, In Su
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (21): : 11092 - 11099
[36] Rh(III)-catalyzed chemoselective C-H functionalizations of tertiary aniline N-oxides with alkynes
Huang, Xiaolei
Liang, Wenbo
Shi, Yang
You, Jingsong
CHEMICAL COMMUNICATIONS, 2016, 52 (37) : 6253 - 6256
[37] Metal-Catalyzed Direct C-H Fluoroalkenylation of Pyridine N-Oxides and Related Derivatives
Lehecq, Alexis
Rousee, Kevin
Schneider, Cedric
Levacher, Vincent
Hoarau, Christophe
Pannecoucke, Xavier
Bouillon, Jean-Philippe
Couve-Bonnaire, Samuel
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (21) : 3049 - 3054
[38] Rhodium(III)-Catalyzed C-H Alkylation/Nucleophilic Addition Domino Reaction
Tang, Mengyao
Li, Yunpeng
Han, Shengnan
Liu, Lei
Ackermann, Lutz
Li, Jie
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (04) : 660 - 664
[39] Reaction Path Determination of Rhodium(I)-Catalyzed C-H Alkylation of N-8-Aminoquinolinyl Aromatic Amides with Maleimides
Taborosi, Attila
He, Oiyuan
Ano, Yusuke
Chatani, Naoto
Mori, Seiji
JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (01): : 737 - 743
[40] Rhodium(III)-Catalyzed C(sp3)-H Alkylation of 8-Methylquinolines with Maleimides
Han, Sangil
Park, Jihye
Kim, Saegun
Lee, Suk Hun
Sharma, Satyasheel
Mishra, Neeraj Kumar
Jung, Young Hoon
Kim, In Su
ORGANIC LETTERS, 2016, 18 (18) : 4666 - 4669

← 1 2 3 4 5 →