Hemin-Catalyzed, Cyclodextrin-Assisted Insertion of Carbenoids into N-H Bonds

被引：23

作者：

Xu, Xiaofei ^{[1
]}

Li, Chang ^{[2
]}

Tao, Zhihao ^{[1
]}

Pan, Yuanjiang ^{[1
]}

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China

[2] Zhejiang Univ, Coll Pharmaceut Sci, Hangzhou 310058, Zhejiang, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2015年 / 357卷 / 14-15期

关键词：

cyclodextrins; diazo compounds; green chemistry; hemin; N-H insertion; DIAZO-COMPOUNDS; IRON PORPHYRIN; ESTERS; WATER; DIAZOACETATES; CORROLES; ANILINES; ACIDS;

D O I：

10.1002/adsc.201500418

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An aqueous hemin-catalyzed, cyclodextrin-assisted N-H insertion reaction of a-diazo ester into aromatic amines is described here. This aqueous catalytic system showed good compatibility with various arylamines, with yields up to 96%. A size-controlled reaction phenomenon by different cyclodextrins (CDs) was also observed when ethyl diazoacetate (EDA) was used. The reaction mechanism was also preliminarily proposed on the basis of designed control experiments.

引用

页码：3341 / 3345

页数：5

共 50 条

[41] Carbene insertion to N-H bonds of 2-aminothiazole and 2-amino-1,3,4-thiadiazole derivatives catalyzed by iron phthalocyanine [J].

Cailler, Lucie P. ;

Martynov, Alexander G. ;

Gorbunova, Yulia G. ;

Tsivadze, Asian Yu ;

Sorokin, Alexander B. .

JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, 2019, 23 (4-5) :497-506

[42] TBAI-Catalyzed S-H and N-H Insertion Reactions of α-Diazoesters with Thiophenols and Amines under Metal-Free Conditions [J].

Chen, Rongxiang ;

Ma, Guoyang ;

Li, Yawen ;

Zhang, Jinju ;

Xia, Ran ;

Wang, Kai-Kai ;

Liu, Lantao .

JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (16) :10990-10999

[43] Rhodium(III)-Catalyzed N-H Insertion Reaction of Phosphoryl Amides withα-ArylDiazoesters for the Synthesis ofα-PhosphorylAmino Esters [J].

Son, Jeong-Yu ;

Baek, Yonghyeon ;

Kim, Sanghyuck ;

Lee, Kyungsup ;

Lee, Phil Ho .

BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2020, 41 (06) :615-627

[44] Asymmetric intermolecular cyclopropanation of alkenes and N-H insertion of aminoesters by diazoacetylferrocene catalyzed by ruthenium and iron porphyrins [J].

Carrie, Daniel ;

Roisnel, Thierry ;

Simonneaux, Gerard .

POLYHEDRON, 2021, 205

[45] Enantioselective Formal Vinylogous N-H Insertion of Secondary Aliphatic Amines Catalyzed by a High-Spin Cobalt(II) Complex [J].

Yang, Wei ;

Pu, Maoping ;

Lin, Xiaobin ;

Chen, Min ;

Song, Yanji ;

Liu, Xiaohua ;

Wu, Yun-Dong ;

Feng, Xiaoming .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (25) :9648-9656

[46] Catalyst-dependent chemoselective insertion of diazoalkanes into the N-H/C-H/O-H/C-O bonds of 2-hydroxybenzothiazoles [J].

Jin, Lvnan ;

Zhou, Xuan ;

Zhao, Yunbo ;

Guo, Jing ;

Stephan, Douglas W. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (39) :7781-+

[47] Borane-Catalyzed, HFIP-Assisted Carbene Insertion into Internal Alkenyl C-H Bonds under Metal-Free Conditions [J].

Huang, Zilong ;

Lin, Jie ;

Ma, Juan ;

Wang, Liandi ;

Zhou, Yong-Gui ;

Yu, Zhengkun .

ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (24) :4333-4346

[48] DFT study on Rh(<sc>ii</sc>)/guanidine-catalyzed asymmetric N-H bond insertion of benzophenone imines [J].

Xu, Jiaying ;

Wei, Qi ;

Hu, Changwei ;

Su, Zhishan .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2025, 23 (12) :2896-2903

[49] Rhodium(II) catalyzed synthesis of macrocycles incorporating oxindole via O-H/N-H insertion reactions [J].

Muthusamy, Sengodagounder ;

Karikalan, Thangaraju .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (45) :9243-9256

[50] Copper-Catalyzed Carbenoid Insertion Reactions of α-Diazoesters and α-Diazoketones into Si-H and S-H Bonds [J].

Keipour, Hoda ;

Jalba, Angela ;

Delage-Laurin, Leo ;

Ollevier, Thierry .

JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (06) :3000-3010

← 1 2 3 4 5 →