Regioselective C3-Phosphonation of Free Indoles via Transition-Metal-Free Radical/Hydrolysis Cascade

被引：11

作者：

Guo, Shengmei ^{[1
]}

Jie, Kun ^{[1
]}

Zhang, Zhebin ^{[1
]}

Fu, Zhengjiang ^{[1
]}

Cai, Hu ^{[1
]}

机构：

[1] Nanchang Univ, Dept Chem, Xuefu Rd 999, Nanchang 330031, Jiangxi, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 2019卷 / 08期

基金：

美国国家科学基金会;

关键词：

Regioselection; C3-phosphonation; Free indoles; Radicals; Hydrolysis; C-H ARYLATION; SELECTIVE ARYLATION; BOND FORMATION; C-3; ARYLATION; ARYL; PHOSPHORYLATION; FUNCTIONALIZATION; PHOSPHONATION; ALKYLATION; ALKALOIDS;

D O I：

10.1002/ejoc.201801889

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The selectivity is of great importance for the preparation of molecules in organic chemistry. Herein, a novel method to enable the highly regioselective C3-phosphonation of free indoles has been developed. This transformation involves a radical and a hydrolysis procedure, and tolerates a range of functional groups, which gives an efficient route toward the 1H-indol-3 - ylphosphonic acid monoesters in one step.

引用

页码：1808 / 1814

页数：7

共 50 条

[1] Transition-Metal-Free C3 Arylation of Indoles with Aryl Halides
Chen, Ji
Wu, Jimmy
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (14) : 3951 - 3955
[2] Transition Metal-Free Regioselective Phosphonation of Pyridines: Scope and Mechanism
Quint, Valentin
Nguyen, Thi Hong Van
Mathieu, Gary
Chelli, Saloua
Breugst, Martin
Lohier, Jean-Francois
Gaumont, Annie-Claude
Lakhdar, Sami
[J]. ACS ORGANIC & INORGANIC AU, 2023, 3 (03): : 151 - 157
[3] Transition-Metal-Free Radical Hydrotrifluoromethylation of Alkynes
Matcha, Kiran
Antonchick, Andrey P.
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (2-3) : 309 - 312
[4] Transition-metal-free cascade reaction of α-halo-N-tosylhydrazones, indoles and arylboronic acids
Wu, Guojiao
Deng, Yifan
Luo, Haiqing
Zhou, Junliang
Li, Tianjiao
Zhang, Yan
Wang, Jianbo
[J]. CHEMICAL COMMUNICATIONS, 2016, 52 (30) : 5266 - 5268
[5] Transition-Metal-Free Borylation of Alkyl Iodides via a Radical Mechanism
Liu, Qianyi
Hong, Junting
Sun, Beiqi
Bai, Guangcan
Li, Feng
Liu, Guoquan
Yang, Yang
Mo, Fanyong
[J]. ORGANIC LETTERS, 2019, 21 (17) : 6597 - 6602
[6] Transition-Metal-Free Radical Borylation Reactions
Shang, Zhi-Hao
Pan, Jun
Wang, Zeyu
Zhang, Ze-Xin
Wu, Jingjing
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (12)
[7] Transition-metal-free chemo- and regioselective vinylation of azaallyls
Minyan Li
Osvaldo Gutierrez
Simon Berritt
Ana Pascual-Escudero
Ahmet Yeşilçimen
Xiaodong Yang
Javier Adrio
Georgia Huang
Eiko Nakamaru-Ogiso
Marisa C. Kozlowski
Patrick J. Walsh
[J]. Nature Chemistry, 2017, 9 : 997 - 1004
[8] Transition-metal-free chemo- and regioselective vinylation of azaallyls
Li, Minyan
Gutierrez, Osvaldo
Berritt, Simon
Pascual-Escudero, Ana
Yesilcimen, Ahmet
Yang, Xiaodong
Adrio, Javier
Huang, Georgia
Nakamaru-Ogiso, Eiko
Kozlowski, Marisa C.
Walsh, Patrick J.
[J]. NATURE CHEMISTRY, 2017, 9 (10) : 997 - 1004
[9] Transition-metal-free and additive-free intermolecular hydroarylation of alkenes with indoles in hexafluoroisopropanol
Zhou, Changsheng
Huang, Ming
Yao, Yufeng
Chen, Chunyu
Yi, Xin
Yang, Ke-fang
Lai, Guo-Qiao
Xuan, Wenjing
Zhang, Pinglu
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (48) : 9534 - 9541
[10] Transition-metal-free regioselective thiocyanation of phenols, anilines and heterocycles
Mete, Trimbak B.
Khopade, Tushar M.
Bhat, Ramakrishna G.
[J]. TETRAHEDRON LETTERS, 2017, 58 (05) : 415 - 418

← 1 2 3 4 5 →