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

[1] Rhodium-Catalysed Enantioselective C-H Functionalization in Asymmetric Synthesis
Motevalli, Somayeh
Sokeirik, Yasser
Ghanem, Ashraf
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (08) : 1459 - 1475
[2] Transition metal catalysed intermolecular C-H amidation of arenes
Kilaru, Praveen
Das, Kushal
Zhao, Pinjing
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 255
[3] Reversed reactivity of anilines with alkynes in the rhodium-catalysed C-H activation/carbonylation tandem
Midya, Siba P.
Sahoo, Manoj K.
Landge, Vinod G.
Rajamohanan, P. R.
Balaraman, Ekambaram
NATURE COMMUNICATIONS, 2015, 6
[4] Combined Experimental and Computational Investigations of Rhodium-Catalysed C-H Functionalisation of Pyrazoles with Alkenes
Algarra, Andres G.
Davies, David L.
Khamker, Qudsia
Macgregor, Stuart A.
McMullin, Claire L.
Singh, Kuldip
Villa-Marcos, Barbara
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (07) : 3087 - 3096
[5] Rhodium-catalysed anomalous dimerization of styrenes involving the cleavage of the ortho C-H bond
Tobisu, Mamoru
Hyodo, Isao
Onoe, Masahiro
Chatani, Naoto
CHEMICAL COMMUNICATIONS, 2008, (45) : 6013 - 6015
[6] Rhodium-catalysed direct C-H allylation of N-sulfonyl ketimines with allyl carbonates
Mei, Shu-Tao
Wang, Nan-Jin
Qin Ouyang
Wei, Ye
CHEMICAL COMMUNICATIONS, 2015, 51 (14) : 2980 - 2983
[7] Rhodium-catalysed direct ortho arylation of 2-arylpyridines with arylstannanes via C-H activation
Oi, S
Fukita, S
Inoue, Y
CHEMICAL COMMUNICATIONS, 1998, (22) : 2439 - 2440
[8] Rhodium(III)-Catalyzed Intermolecular N-Chelator-Directed Aromatic C-H Amidation with Amides
Zhao, Huaiqing
Shang, Yaping
Su, Weiping
ORGANIC LETTERS, 2013, 15 (19) : 5106 - 5109
[9] Rhodium-catalysed direct hydroarylation of alkenes and alkynes with phosphines through phosphorous-assisted C-H activation
Wang, Dingyi
Dong, Ben
Wang, Yandong
Qian, Jiasheng
Zhu, Jinjun
Zhao, Yue
Shi, Zhuangzhi
NATURE COMMUNICATIONS, 2019, 10 (1)
[10] Rhodium-Catalysed Selective C-H Allylation of 1H-Indazoles with Vinylethylene Carbonate: Easily Introducing Allylic Alcohol
Zhao, Xiang
Huang, Junwei
Feng, Yadong
Cui, Xiuling
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (40)

← 1 2 3 4 5 →