Microwave-Assisted Cp*CoIII-Catalyzed C-H Activation/Double C-N Bond Formation Reactions to Thiadiazine 1-Oxides

被引：102

作者：

Huang, Jiapian ^{[1
]}

Huang, Yangfei ^{[1
]}

Wang, Tao ^{[1
]}

Huang, Qin ^{[1
]}

Wang, Zhihua ^{[1
]}

Chen, Zhiyuan ^{[1
]}

机构：

[1] Jiangxi Normal Univ, Coll Chem & Chem Engn, Key Lab Funct Small Organ Mol, Minist Educ, 99 Ziyang Rd, Nanchang 330022, Jiangxi, Peoples R China

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 05期

基金：

中国国家自然科学基金;

关键词：

ALKYNYLATED SULFOXIMINES; REACTIVITY; DERIVATIVES; AMIDATION; QUINAZOLINES; SULFOXIDES; OXIDATION; ARENES; ACIDS;

D O I：

10.1021/acs.orglett.7b00120

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A microwave-assisted, Cp*Co-III-catalyzed direct C-H activation/double C-N bond formation reaction of simple NH-sulfoximines with 1,4,2-dioxazol-5-ones to produce diverse thiadiazine-1-oxides is reported. The reaction tolerates a broad range of functional groups under external oxidant-free conditions and only releases CO2 and H2O as the sole byproducts. The preliminary mechanistic studies revealed an electrophilic

引用

页码：1128 / 1131

页数：4

共 50 条

[31] Recent advances in the transition metal-catalyzed twofold oxidative C-H bond activation strategy for C-C and C-N bond formation
Cho, Seung Hwan
Kim, Ji Young
Kwak, Jaesung
Chang, Sukbok
CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) : 5068 - 5083
[32] Electrochemical strategies for C-H functionalization and C-N bond formation
Karkas, Markus D.
CHEMICAL SOCIETY REVIEWS, 2018, 47 (15) : 5786 - 5865
[33] C-H imidation: a distinct perspective of C-N bond formation
Rit, Raja K.
Shankar, Majji
Sahoo, Akhila K.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (06) : 1282 - 1293
[34] Cascade synthesis of azoquinazolinones by Cu(I)-catalyzed C-N coupling/C-H activation/C-N formation reactions under O2
Chen, Dingben
Chen, Qiufang
Liu, Miaochang
Dai, Shuangqun
Huang, Ling
Yang, Jianguo
Bao, Weiliang
TETRAHEDRON, 2013, 69 (31) : 6461 - 6467
[35] Rh(III)-Catalyzed C(8)-H Activation of Quinoline N-Oxides: Regioselective C-Br and C-N Bond Formation
Dhiman, Ankit Kumar
Gupta, Shiv Shankar
Sharma, Ritika
Kumar, Rakesh
Sharma, Upendra
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (20): : 12871 - 12880
[36] Stable Pd-nanoparticles catalyzed domino C-H activation/C-N bond formation strategy: An access to phenanthridinones
Saha, Rajib
Sekar, Govindasamy
JOURNAL OF CATALYSIS, 2018, 366 : 176 - 188
[37] Concerted C-N/C-H Bond Formation in Highly Enantioselective Yttrium(III)-Catalyzed Hydroamination
Manna, Kuntal
Kruse, Marissa L.
Sadow, Aaron D.
ACS CATALYSIS, 2011, 1 (11): : 1637 - 1642
[38] 3d-transition metal catalyzed C-H to C-N bond formation: An update
Singh, Ritesh
Sathish, Elagandhula
Gupta, Ashis K.
Goyal, Sophiya
TETRAHEDRON, 2021, 100
[39] Cooperative Lewis Acid/Cp*CoIII Catalyzed C-H Bond Activation for the Synthesis of Isoquinolin-3-ones
Kim, Ju Hyun
Gressies, Steffen
Glorius, Frank
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (18) : 5577 - 5581
[40] Copper-catalyzed C-N bond formation through C-H/N-H activation: a novel approach to the synthesis of multisubstituted ureas
Jiang, Honglai
Lin, Aijun
Zhu, Chengjian
Cheng, Yixiang
CHEMICAL COMMUNICATIONS, 2013, 49 (08) : 819 - 821

← 1 2 3 4 5 →