Copper-Mediated Oxidative Functionalization of C(sp3)-H Bonds with Isoquinolines: Two-Step Synthesis of 5-Oxaprotoberberinones

被引：2

作者：

Wang, Dingyi ^{[1
]}

Zhang, Rongxing ^{[1
]}

Deng, Ruihong ^{[1
]}

Lin, Sen ^{[1
]}

Guo, Shengmei ^{[1
]}

Yan, Zhaohua ^{[1
]}

机构：

[1] Nanchang Univ, Coll Chem, Nanchang 330031, Jiangxi, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 22期

基金：

中国国家自然科学基金;

关键词：

C-H AMINATION; EFFICIENT SYNTHESIS; METAL-FREE; AMIDATION; HYDROCARBONS; CYCLIZATION; ROSETTACIN; ACTIVATION; ANNULATION; ALKALOIDS;

D O I：

10.1021/acs.joc.6b02145

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A copper-mediated oxidative functionalization of C(sp(3))-H bonds with isoquinolines via a radical process without ligands was achieved. The present system exhibits a novel pathway for the preparation of N-alkyl (benzyl) isoquinolin-1(2H)-ones in moderate to high yields. In addition, this procedure provides a simple method to afford 5-oxaprotoberberinones and their derivatives in two steps.

引用

页码：11162 / 11167

页数：6

共 50 条

[1] Copper-Mediated Dehydrogenative C(sp3)-H Borylation of Alkanes
Sang, Ruocheng
Han, Wangyujing
Zhang, Hanwen
Saunders, Carla M.
Noble, Adam
Aggarwal, Varinder K.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (28) : 15207 - 15217
[2] Copper-Mediated Direct C(sp3)-H and C(sp2)-H Acetoxylation
Wang, Zhen
Kuninobu, Yoichiro
Kanai, Motomu
ORGANIC LETTERS, 2014, 16 (18) : 4790 - 4793
[3] Mechanosynthesis of Fullerotetrahydroquinolines by Copper-Mediated sp3 C-H Functionalization of N,N -Dimethylanilines with [60]Fullerene
Yang, Huan
Ye, Shi-Qi
Shao, Gang
Chen, Jun-Shen
Wang, Guan-Wu
SYNLETT, 2023, 34 (17) : 2047 - 2051
[4] Carbodicarbene-Stibenium Ion-Mediated Functionalization of C(sp3)-H and C(sp)-H Bonds
Warring, Levi
Westendorff, Karl S.
Bennett, Marc T.
Nam, Kijeong
Stewart, Brennan M.
Dickie, Diane A.
Paolucci, Christopher
Gunnoe, T. Brent
Gilliard, Robert J.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2025, 64 (03)
[5] Photocatalyzed Enantioselective Functionalization of C(sp3)-H Bonds
Xu, Guo-Qiang
Wang, Wei David
Xu, Peng-Fei
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (02) : 1209 - 1223
[6] A catalytic approach for the functionalization of C(sp3)-H bonds
Tobisu, M
Chatani, N
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (11) : 1683 - 1684
[7] Mechanistic insights into copper-mediated benzylic C(sp3)-H bond trifluoromethylation
Chen, Xiahe
Liu, Hang
Ding, Debo
Li, Huiling
She, Yuanbin
Yang, Yun-Fang
ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (42) : 8480 - 8487
[8] Copper-Mediated Aryloxylation and Vinyloxylation of β-C(sp3)-H Bond of Propionamides with Organosilanes
Zhang, Jitan
Chen, Hui
Wang, Binjie
Liu, Zhanxiang
Zhang, Yuhong
ORGANIC LETTERS, 2015, 17 (11) : 2768 - 2771
[9] Synthesis of Lactones via C-H Functionalization of Nonactivated C(sp3)-H Bonds
Richers, Johannes
Heilmann, Michael
Drees, Markus
Tiefenbacher, Konrad
ORGANIC LETTERS, 2016, 18 (24) : 6472 - 6475
[10] Recent Advances in Copper-Catalyzed Functionalization of Unactivated C(sp3)-H Bonds
Deshpande, Neha
Satani, Piyushkumar
Bharodiya, Akshay
Naveen, Togati
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (12)

← 1 2 3 4 5 →