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

[41] Highly Selective Rhodium Catalyzed Domino C-H Activation/Cyclizations [J].

Tran, Duc N. ;

Cramer, Nicolai .

CHIMIA, 2011, 65 (04) :271-273

[42] Enantioselective, intermolecular benzylic C-H amination catalysed by an engineered iron-haem enzyme [J].

Prier, Christopher K. ;

Zhang, Ruijie K. ;

Buller, Andrew R. ;

Brinkmann-Chen, Sabine ;

Arnold, Frances H. .

NATURE CHEMISTRY, 2017, 9 (07) :629-634

[43] A rhodium-catalysed three-component reaction to access C1-substituted tetrahydroisoquinolines [J].

Zhang, Dan ;

Liu, Junwen ;

Kang, Zhenghui ;

Qiu, Huang ;

Hu, Wenhao .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (46) :9844-9848

[44] Photochemical features of intermolecular C-H bond activation [J].

Lees, AJ .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1998, 554 (01) :1-11

[45] A Convenient Photocatalytic Fluorination of Unactivated C-H Bonds [J].

Halperin, Shira D. ;

Fan, Hope ;

Chang, Stanley ;

Martin, Rainer E. ;

Britton, Robert .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (18) :4690-4693

[46] Indazolones Directed Rh(III)-Catalyzed C-H Amidation of Arenes [J].

Chen, Shao-Yong ;

Zheng, Yi-Chuan ;

Liu, Xu-Ge ;

Song, Jia-Lin ;

Shu, Bing ;

Zheng, Tao ;

Xiao, Lin ;

Zhang, Shang-Shi ;

Cao, Hua .

ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (18) :3302-3309

[47] Oxazolinyl-Assisted C-H Amidation by Cobalt(III) Catalysis [J].

Mei, Ruhuai ;

Loup, Joachim ;

Ackermann, Lutz .

ACS CATALYSIS, 2016, 6 (02) :793-797

[48] A silver-catalyzed intramolecular amidation of saturated C-H bonds [J].

Cui, Y ;

He, C .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (32) :4210-4212

[49] Regioselective Intermolecular Allylic C-H Amination of Disubstituted Olefins via Rhodium/π-Allyl Intermediates [J].

Burman, Jacob S. ;

Blakey, Simon B. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (44) :13666-13669

[50] Rhodium(I)-Catalyzed Enantioselective C(sp3)-H Functionalization via Carbene-Induced Asymmetric Intermolecular C-H Insertion† [J].

Liu, Bo ;

Xu, Ming-Hua .

CHINESE JOURNAL OF CHEMISTRY, 2021, 39 (07) :1911-1915

← 1 2 3 4 5 →