Story of an Age-Old Reagent: An Electrophilic Chlorination of Arenes and Heterocycles by 1-Chloro-1,2-benziodoxol-3-one

被引：93

作者：

Wang, Mengzhou ^{[1
]}

Zhang, Yanyan ^{[1
]}

Wang, Tao ^{[1
]}

Wang, Chao ^{[1
]}

Xue, Dong ^{[1
]}

Xiao, Jianliang ^{[1
,2
]}

机构：

[1] Shaanxi Normal Univ, Key Lab Appl Surface & Colloid Chem, Minist Educ, Sch Chem & Chem Engn, Xian 710062, Peoples R China

[2] Univ Liverpool, Dept Chem, Liverpool L69 7ZD, Merseyside, England

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 09期

基金：

中国国家自然科学基金; 英国工程与自然科学研究理事会;

关键词：

HYPERVALENT IODINE REAGENTS; C-H HALOGENATION; IODOBENZENE DICHLORIDE; POLYVALENT IODINE; BODIPY DYES; AROMATIC-COMPOUNDS; DIRECTING-GROUP; PET TRACERS; ALKYNYLATION; DERIVATIVES;

D O I：

10.1021/acs.orglett.6b00547

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

By the use of 1-chloro-1,2-benziodoxol-3-one, an age-old reagent, the practical and efficient chlorination method is achieved. This hypervalent iodine reagent is amenable not only to the chlorination of nitrogen-containing heterocycles but also to selected classes of arenes, BODIPY dyes, and pharmaceuticals. In addition, the advantages, such as easy preparation and recyclable, air- and moisture-stable, in combination with the success in a gram-scale experiment grant this reagent great potential for industrial application.

引用

页码：1976 / 1979

页数：4

共 13 条

[1] Electrophilic chloro(ω-alkoxy)lation of alkenes employing 1-chloro-1,2-benziodoxol-3-one: facile synthesis of β-chloroethers
Jia, Yimin
Chen, Long
Zhang, Huaibin
Zheng, Ying
Jiang, Zhong-Xing
Yang, Zhigang
ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (39) : 7203 - 7213
[2] Regioselective Chlorination of Aryl C-H bonds with Hypervalent Iodine(III) Reagent 1-Chloro-1,2-benziodoxol-3-one
Parvathaneni, Sai Prathima
Perumgani, Pullaiah C.
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (02) : 324 - 327
[3] Chlorination of phenylallene derivatives with 1-chloro-1,2-benziodoxol-3-one: synthesis of vicinal-dichlorides and chlorodienes
Zhao, Zhensheng
Murphy, Graham K.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2018, 14 : 796 - 802
[4] Revisiting 1-chloro-1,2-benziodoxol-3-one: efficient ortho-chlorination of aryls under aqueous conditions
Vinayak, Botla
Ravindrakumar, Pardhi Vishal
Ramana, Daggupati V.
Chandrasekharam, Malapaka
NEW JOURNAL OF CHEMISTRY, 2018, 42 (11) : 8953 - 8959
[5] An improved, scalable synthesis of Notum inhibitor LP-922056 using 1-chloro-1,2-benziodoxol-3-one as a superior electrophilic chlorinating agent
Willis, Nicky J.
Bayle, Elliott D.
Papageorgiou, George
Steadman, David
Aktinson, Benjamin N.
Mahy, William
Fish, Paul, V
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2019, 15 : 2790 - 2797
[6] Utilizing 1-chloro-1,2-benziodoxol-3(1H)-one in the preparation of branched polymers
Kumar, Rajesh
Tsarevsky, Nicolay
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 252
[7] Thiocyanation of Aromatic and Heteroaromatic Compounds with 1-Chloro-1,2-benziodoxol-3-(1H)-one and (Trimethylsilyl)isothiocyanate
Ito, Yuta
Touyama, Akihiro
Uku, Minako
Egami, Hiromichi
Hamashima, Yoshitaka
CHEMICAL & PHARMACEUTICAL BULLETIN, 2019, 67 (09) : 1015 - 1018
[8] A highly efficient TEMPO mediated oxidation of sugar primary alcohols into uronic acids using 1-chloro-1,2-benziodoxol-3(1H)-one at room temperature
Tiwari, Varsha
Badavath, Vishnu Nayak
Singh, Adesh Kumar
Kandasamy, Jeyakumar
TETRAHEDRON LETTERS, 2018, 59 (26) : 2511 - 2514
[9] Difunctionalization of Alkenes Using 1-Chloro-1,2-benziodoxo1-3-(1H)-one
Egami, Hiromichi
Yoneda, Takahiro
Uku, Minako
Ide, Takafumi
Kawato, Yuji
Hamashima, Yoshitaka
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (10): : 4020 - 4030
[10] Ethynyl-1,2-benziodoxol-3(1H)-one (EBX): An Exceptional Reagent for the Ethynylation of Keto, Cyano, and Nitro Esters
Gonzalez, Davinia Fernandez
Brand, Jonathan P.
Waser, Jerome
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (31) : 9457 - 9461

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