Enantioselective Synthesis of Azoniahelicenes by Rh-Catalyzed C-H Annulation with Alkynes

被引：94

作者：

Wang, Qiang ^{[1
]}

Zhang, Wen-Wen ^{[2
]}

Zheng, Chao ^{[1
]}

Gu, Qing ^{[1
]}

You, Shu-Li ^{[1
,2
]}

机构：

[1] Univ Chinese Acad Sci, Chinese Acad Sci, Ctr Excellence Mol Synth, Shanghai Inst Organ Chem,State Key Lab Organometa, Shanghai 200032, Peoples R China

[2] East China Normal Univ, Chang Kung Chuang Inst, Shanghai 200062, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2021年 / 143卷 / 01期

基金：

中国博士后科学基金; 国家重点研发计划;

关键词：

ONE HUNDRED YEARS; NONLINEAR-OPTICAL PROPERTIES; STEREOSELECTIVE SYNTHESES; BOND FUNCTIONALIZATIONS; 2+2+2 CYCLOADDITION; HELICENES; LIGANDS; BINDING; CARBOXYLATE; ACTIVATION;

D O I：

10.1021/jacs.0c11735

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A rhodium(III)-catalyzed enantioselective C-H activation/annulation process is disclosed. With a catalyst derived from a chiral CpRh(III) complex and a chiral acid, the direct annulation reactions between 1-aryl isoquinoline derivatives and alkynes take place smoothly to afford a series of chiral azoniahelicenes in excellent yields and enantioselectivity (up to 99% yield and 96% ee). Mechanistic studies suggest that C-H bond cleavage may be the turnover-limiting step.

引用

页码：114 / 120

页数：7

共 50 条

[21] Rh-Catalyzed C-H Activation/Annulation of Enaminones and Cyclic 1,3-Dicarbonyl Compounds: An Access to Isocoumarins
Wang, Qian
Li, Ying
Sun, Jina
Chen, Shiyu
Li, Hui
Zhou, Yu
Li, Jian
Liu, Hong
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (09) : 5348 - 5358
[22] Rh-Catalyzed oxidative C-H activation/annulation: converting anilines to indoles using molecular oxygen as the sole oxidant
Zhang, Guoying
Yu, Hui
Qin, Guiping
Huang, Hanmin
CHEMICAL COMMUNICATIONS, 2014, 50 (33) : 4331 - 4334
[23] Rh(iii)-Catalyzed C-H activation/annulation of salicylaldehydes with sulfoxonium ylides for the synthesis of chromones
Cai, Libo
Zhu, Xiaoyi
Chen, Jiayi
Lin, Aijun
Yao, Hequan
ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (21): : 3688 - 3692
[24] Cobalt-catalyzed C-H annulation of N-aroylpicolinamides with alkynes for (NH)-isoquinolones synthesis
Wang, Siqi
Yao, Lingyun
Wang, Jian-Shu
Ying, Jun
Wu, Xiao-Feng
MOLECULAR CATALYSIS, 2022, 524
[25] Rh-Catalyzed Intermolecular Carbenoid Functionalization of Aromatic C-H Bonds by α-Diazomalonates
Chan, Wai-Wing
Lo, Siu-Fung
Zhou, Zhongyuan
Yu, Wing-Yiu
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (33) : 13565 - 13568
[26] Synthesis of highly fluorescent helical quinolizinium salts by a Rh-catalyzed cyclotrimerization/C-H activation sequence
Cadart, Timothee
Feriancova, Lucia
Henke, Petr
Gyepes, Robert
Cisarova, Ivana
Kalikova, Kveta
Kotora, Martin
CHEMICAL COMMUNICATIONS, 2025, 61 (24) : 4662 - 4665
[27] Synthesis of Non-canonical Tryptophan Variants via Rh-catalyzed C-H Functionalization of Anilines
Huang, Jonathan Z.
Ying, Vanessa Y.
Seyedsayamdost, Mohammad R.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2025, 64 (02)
[28] Recent advances in Rh(I)-catalyzed enantioselective C-H functionalization
Zhang, Yue
Zhang, Jing-Jing
Lou, Lujun
Lin, Ruofan
Cramer, Nicolai
Wang, Shou-Guo
Chen, Zhen
CHEMICAL SOCIETY REVIEWS, 2024, 53 (07) : 3457 - 3484
[29] Rh(III)-Catalyzed C-H Activation/Annulation for the Construction of Quinolizinones and Indolizines
Hou, Xinjiao
Wang, Run
Fang, Feifei
Qu, Zhiyan
Zhou, Jianhui
Yu, Ting
Wang, Dechuan
Liu, Hong
Zhou, Yu
ORGANIC LETTERS, 2024, 26 (21) : 4451 - 4456
[30] Rh(III)-Catalyzed Sequential C-H Amination/Annulation Cascade Reactions: Synthesis of Multisubstituted Benzimidazoles
Huang, Siqi
Li, Huan
Sun, Xiangying
Xu, Linhua
Wang, Lianhui
Cui, Xiuling
ORGANIC LETTERS, 2019, 21 (14) : 5570 - 5574

← 1 2 3 4 5 →