Oxidative Ritter-type Chloroamidation of Alkenes Using NaCl and Oxone

被引：6

作者：

Kato, Takehiro ^{[1
]}

Okada, Yuya ^{[1
]}

Fujii, Yuto ^{[1
]}

Uyanik, Muhammet ^{[1
]}

Ishihara, Kazuaki ^{[1
]}

机构：

[1] Nagoya Univ, Grad Sch Engn, Chikusa Ku, Nagoya, Aichi 4648603, Japan

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 10卷 / 11期

关键词：

alkene; styrene; chloroamidation; oxidation; oxone; ONE-POT SYNTHESIS; RESONANCE-SPECTROSCOPY; SELECTIVE OXIDATION; CARBOXYLIC-ACIDS; HALONIUM IONS; OLEFINS; CHLORINATION; HALOGENATION; CONVENIENT; ADDITIONS;

D O I：

10.1002/ajoc.202100575

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report a practical and environmentally benign method for the oxidative Ritter-type chloroamidation of alkenes using sodium chloride and oxone as a chlorinating source and an oxidant, respectively, in acetonitrile under mild conditions. The reaction proceeded smoothly under non-aqueous conditions without the use of any catalyst. Excellent chemoselectivity (i. e., chloroamidation versus dichlorination) could be achieved for electron-deficient styrenes. In addition, this protocol could be easily applied to 7-gram-scale synthesis.

引用

页码：2907 / 2910

页数：4

共 50 条

[1] Ritter-type reactions of N-chlorosaccharin:: A method for the electrophilic diamination of alkenes
Booker-Milburn, KI
Guly, DJ
Cox, B
Procopiou, PA
ORGANIC LETTERS, 2003, 5 (18) : 3313 - 3315
[2] Ritter-type fluorofunctionalisation as a new, effective method for conversion of alkenes to vicinal fluoroamides
Stavber, S
Pecan, TS
Papez, M
Zupan, M
CHEMICAL COMMUNICATIONS, 1996, (19) : 2247 - 2248
[3] Copper-Catalyzed Ritter-Type Reaction of Unactivated Alkenes with Dichloramine-T
Abe, Takumi
Takeda, Hiroyuki
Miwa, Yoshihisa
Yamada, Koji
Yanada, Reiko
Ishikura, Minoru
HELVETICA CHIMICA ACTA, 2010, 93 (02) : 233 - 241
[4] Electrochemical Oxidative C-H Amination through a Ritter-Type Reaction
Xu, Yiwen
Li, Qiang
Ye, Runyou
Xu, Buyi
Zhou, Xiangge
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (13): : 9518 - 9522
[5] Regioselective Oxidative Chlorination of Arenols Using NaCl and Oxone
Uyanik, Muhammet
Sahara, Naoto
Ishihara, Kazuaki
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (01) : 27 - 31
[6] Ritter-type amidation of alkylboron derivatives with nitriles
Cazorla, Clement
Metay, Estelle
Andrioletti, Bruno
Lemaire, Marc
TETRAHEDRON LETTERS, 2009, 50 (49) : 6855 - 6857
[7] Hypervalent iodine-mediated Ritter-type amidation of terminal alkenes: The synthesis of isoxazoline and pyrazoline cores
Park, Sang Won
Kim, Soong-Hyun
Song, Jaeyoung
Park, Ga Young
Kim, Darong
Nam, Tae-Gyu
Hong, Ki Bum
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2018, 14 : 1028 - 1033
[8] Exploration of Oxidative Ritter-Type Reaction of α-Arylketones and Its Application for the Collective Total Syntheses of Erythrina Alkaloids
Chen, Meng-En
Tang, Shi-Zhong
Hu, Yue-Hong
Li, Qin-Tong
Gan, Zhang-Yan
Lv, Jian-Wei
Zhang, Fu-Min
CCS CHEMISTRY, 2022, 4 (10): : 3378 - 3390
[9] First Ritter-type reaction of alkylbenzenes using N-hydroxyphthalimide as a key catalyst
Sakaguchi, S
Hirabayashi, T
Ishii, Y
CHEMICAL COMMUNICATIONS, 2002, (05) : 516 - 517
[10] ISOQUINOLINE DERIVATIVES FROM THE RITTER-TYPE REACTION OF VINYL CATIONS
KITAMURA, T
KOBAYASHI, S
TANIGUCHI, H
CHEMISTRY LETTERS, 1984, (08) : 1351 - 1354

← 1 2 3 4 5 →