Transition-metal-free synthesis of 3-sulfenylated chromones via KIO3-catalyzed radical C(sp2)-H sulfenylation

被引：35

作者：

Guo, Yanhui ^{[1
]}

Zhong, Shanshan ^{[1
]}

Wei, Li ^{[1
]}

Wan, Jie-Ping ^{[1
]}

机构：

[1] Jiangxi Normal Univ, Coll Chem & Chem Engn, Nanchang 330022, Jiangxi, Peoples R China

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 13卷

基金：

中国国家自然科学基金;

关键词：

C-H sulfenylation; chromones; domino reaction; free-radical; transition-metal-free; S BOND FORMATION; CATALYZED CARBONYLATIVE SYNTHESIS; IODINE-MEDIATED SYNTHESIS; CROSS-COUPLING REACTIONS; C-H SULFENYLATION; REGIOSELECTIVE SULFENYLATION; ROOM-TEMPERATURE; SULFONYL HYDRAZIDES; AMMONIUM IODIDE; FUNCTIONALIZATION;

D O I：

10.3762/bjoc.13.199

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reactions between o-hydroxylphenyl-functionalized enaminones and sulfonyl hydrazines providing 3-sulfenylated chromones via domino chromone ring construction and C(sp(2))-H bond sulfenylation have been achieved under transition-metal-free conditions by using KIO3 as the only catalyst.

引用

页码：2017 / 2022

页数：6

共 49 条

[1] Copper in cross-coupling reactions - The post-Ullmann chemistry [J].

Beletskaya, IP ;

Cheprakov, AV .

COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364

[2] Transition-Metal-Catalyzed C-S, C-Se, and C-Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions [J].

Beletskaya, Irina P. ;

Ananikov, Valentine P. .

CHEMICAL REVIEWS, 2011, 111 (03) :1596-1636

[3] Rearranged limonoids and chromones from Harrisonia perforata and their anti-inflammatory activity [J].

Choodej, Siwattra ;

Sommit, Damrong ;

Pudhom, Khanitha .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (13) :3896-3900

[4]

Damani L.A., 1989, Sulphur Containing Drugs and Related Organic Compounds

[5] Disulfide-Catalyzed Visible-Light-Mediated Oxidative Cleavage of C=C Bonds and Evidence of an Olefin-Disulfide Charge-Transfer Complex [J].

Deng, Yuchao ;

Wei, Xiao-Jing ;

Wang, Hui ;

Sun, Yuhan ;

Noel, Timothy ;

Wang, Xiao .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (03) :832-836

[6] Iodine-mediated synthesis of sulfur-bridged enaminones and chromones via double C(sp2)-H thiolation [J].

Gao, Yong ;

Wei, Li ;

Liu, Yunyun ;

Wan, Jie-Ping .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (21) :4631-4634

[7] Iodine-catalyzed oxidative system for 3-sulfenylation of indoles with disulfides using DMSO as oxidant under ambient conditions in dimethyl carbonate [J].

Ge, Wenlei ;

Wei, Yunyang .

GREEN CHEMISTRY, 2012, 14 (07) :2066-2070

[8] Synthesis of Succinimide-Containing Chromones, Naphthoquinones, and Xanthones under Rh(III) Catalysis: Evaluation of Anticancer Activity [J].

Han, Sang Hoon ;

Kim, Saegun ;

De, Umasankar ;

Mishra, Neeraj Kumar ;

Park, Jihye ;

Sharma, Satyasheel ;

Kwak, Jong Hwan ;

Han, Sangil ;

Kim, Hyung Sik ;

Kim, In Su .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (24) :12416-12425

[9] Synthesis of Aryl Sulfides: Metal-Free C-H Sulfenylation of Electron-Rich Arenes [J].

Hostier, Thomas ;

Ferey, Vincent ;

Ricci, Gino ;

Pardo, Domingo Gomez ;

Cossy, Janine .

ORGANIC LETTERS, 2015, 17 (15) :3898-3901

[10] Radical-Radical Cross-Coupling for C-S Bond Formation [J].

Huang, Zhiliang ;

Zhang, Dongchao ;

Qi, Xiaotian ;

Yan, Zhiyuan ;

Wang, Mengfan ;

Yang, Haiming ;

Lei, Aiwen .

ORGANIC LETTERS, 2016, 18 (10) :2351-2354

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