Dibenzothiophenesulfilimines: A Convenient Approach to Intermolecular Rhodium-Catalysed C-H Amidation

被引：18

作者：

Antoni, Patrick W. ^{[1
]}

Mackenroth, Alexandra V. ^{[1
]}

Mulks, Florian F. ^{[1
]}

Rudolph, Matthias ^{[1
]}

Helmchen, Guenter ^{[1
]}

Hashmi, A. Stephen K. ^{[1
,2
]}

机构：

[1] Heidelberg Univ, Inst Organ Chem, Neuenheimer Feld 270, D-69120 Heidelberg, Germany

[2] King Abdulaziz Univ, Fac Sci, Chem Dept, Jeddah 21589, Saudi Arabia

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2020年 / 26卷 / 37期

关键词：

amidation; C-H activation; homogeneous catalysis; rhodium; sulfilimines; transition-metal catalysis; BOND-FORMING REACTIONS; PHOTOCHEMISTRY; ANNULATION; ANTHRANILS; ACCESS;

D O I：

10.1002/chem.202002371

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A sulfilimine-based Group 9 transition-metal-catalysed C-H amidation procedure is reported. Dibenzothiophene-based sulfilimines were shown to constitute a class of novel amidation reagents which enable the transfer of a wide range of N-sulfonyl and N-acyl moieties. It was demonstrated that sulfilimines, which are easily accessible from cheap reagents, are safe-to-handle and represent broadly applicable amidation reagents. The dibenzothiophene can be recycled after use. The C-H amidation was shown to proceed with high selectivity and gave the mono-amidated products, mostly in good to excellent yields.

引用

页码：8235 / 8238

页数：4

共 50 条

[21] Palladium-Catalyzed Intermolecular Directed C-H Amidation of Aromatic Ketones
Xiao, Bin
Gong, Tian-Jun
Xu, Jun
Liu, Zhao-Jing
Liu, Lei
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (05) : 1466 - 1474
[22] Ru(II)-catalyzed intermolecular C-H amidation of weakly coordinating ketones
Zheng, Qing-Zhong
Liang, Yu-Feng
Qin, Chong
Jiao, Ning
CHEMICAL COMMUNICATIONS, 2013, 49 (50) : 5654 - 5656
[23] Palladium-catalyzed intermolecular C-H amidation of indoles with sulfonyl azides
Ziwei Hu
Shuang Luo
Qiang Zhu
Science China Chemistry, 2015, 58 : 1349 - 1353
[24] Rhodium-Catalyzed Intermolecular Amidation of Arenes with Sulfonyl Azides via Chelation-Assisted C-H Bond Activation
Kim, Ji Young
Park, Sae Hume
Ryu, Jaeyune
Hwan, Seung Cho
Kim, Seok Hwan
Chang, Sukbok
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (22) : 9110 - 9113
[25] Palladium-catalyzed intermolecular C-H amidation of indoles with sulfonyl azides
Hu, Ziwei
Luo, Shuang
Zhu, Qiang
SCIENCE CHINA-CHEMISTRY, 2015, 58 (08) : 1349 - 1353
[26] Efficient diastereoselective intermolecular rhodium-catalyzed C-H amination
Liang, Chungen
Robert-Pedlard, Fabien
Fruit, Corinne
Mueller, Paul
Dodd, Robert H.
Dauban, Philippe
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (28) : 4641 - 4644
[27] Asymmetric amidation of saturated C-H bonds catalysed by chiral ruthenium and manganese porphyrins
Zhou, XG
Yu, XQ
Huang, JS
Che, CM
CHEMICAL COMMUNICATIONS, 1999, (23) : 2377 - 2378
[28] Replacing dichloroethane as a solvent for rhodium-catalysed intermolecular alkyne hydroacylation reactions: the utility of propylene carbonate
Lenden, Philip
Ylioja, Paul M.
Gonzalez-Rodriguez, Carlos
Entwistle, David A.
Willis, Michael C.
GREEN CHEMISTRY, 2011, 13 (08) : 1980 - 1982
[29] Mechanochemical Rhodium-Catalyzed C-H Bond Amidation of Ferrocenes by Ball Milling
Li, Hao
Ma, Tongtong
Wang, Yingxin
Wang, Bosen
Li, Dianjun
Yang, Jinhui
CHEMISTRY-AN ASIAN JOURNAL, 2023, 18 (14)
[30] Iridium(III)-Catalyzed Intermolecular Allylic C-H Amidation of Internal Alkenes with Sulfonamides
Sihag, Pinki
Jeganmohan, Masilamani
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (20): : 13053 - 13064

← 1 2 3 4 5 →