Pd-catalyzed dehydrogenative annulation approach for the efficient synthesis of phenanthridinones

被引：70

作者：

Li, Xinyao ^{[1
]}

Pan, Jun ^{[1
]}

Song, Song ^{[1
]}

Jiao, Ning ^{[1
,2
]}

机构：

[1] Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Xue Yuan Rd 38, Beijing 100191, Peoples R China

[2] Nankai Univ, State Key Lab Elementoorgan Chem, Weijin Rd 94, Tianjin 300071, Peoples R China

来源：

CHEMICAL SCIENCE | 2016年 / 7卷 / 08期

基金：

中国国家自然科学基金;

关键词：

CATELLANI ORTHO-ARYLATION; H BOND ACTIVATION; C-H; ARYL IODIDES; N-METHOXYBENZAMIDES; SIMPLE ANILINES; INDOLES; CASCADE; ALKYNES; ARENES;

D O I：

10.1039/c6sc01148a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel Pd-catalyzed intermolecular dehydrogenative annulation of aryl iodides and aryl carbamic chlorides for the efficient synthesis of phenanthridinone derivatives was developed. Simple aryl iodides and carbamic chlorides readily made from various anilines, a broad substrate scope with hetero/polycycles, as well as high-value products, make this direct dehydrogenative annulation approach very practical and attractive.

引用

页码：5384 / 5389

页数：6

共 50 条

[1] Pd-Catalyzed [3+2]-Dehydrogenative Annulation Reactions
Liu, Yang
La Roch, Mikael
Mori, Alessia
Pradal, Alexandre
Poli, Giovanni
Oble, Julie
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (38)
[2] Nongaseous Pd-catalyzed carbonylative annulation: Safe and atomic efficient flavone synthesis
Guo, Meng
Wu, Dou
Yang, Hongyu
Zhang, Xiao
Gao, Ziwei
Jian, Yajun
Xue, Dongxu
Zhang, Weiqiang
[J]. MOLECULAR CATALYSIS, 2024, 555
[3] Synthesis of Fluorenone Derivatives through Pd-Catalyzed Dehydrogenative Cyclization
Li, Hu
Zhu, Ru-Yi
Shi, Wen-Juan
He, Ke-Han
Shi, Zhang-Jie
[J]. ORGANIC LETTERS, 2012, 14 (18) : 4850 - 4853
[4] Efficient synthesis of anthranilic esters via Pd-catalyzed dehydrogenative/decarbonylative coupling of anilides and glyoxylates
Wang, Sizhuo
Yang, Zhiyong
Liu, Jidan
Xie, Kai
Wang, Anwei
Chen, Xiang
Tan, Ze
[J]. CHEMICAL COMMUNICATIONS, 2012, 48 (79) : 9924 - 9926
[5] Synthesis of polycyclic aromatic hydrocarbons by the Pd-catalyzed annulation of alkynes
Larock, RC
Doty, MJ
Tian, QP
Zenner, JM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (22): : 7536 - 7537
[6] A Cross-Dehydrogenative Annulation Strategy towards Synthesis of Polyfluorinated Phenanthridinones with Copper
Mandal, Anup
Selvakumar, Jayaraman
Dana, Suman
Mukherjee, Upasana
Baidya, Mahiuddin
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (14) : 3448 - 3454
[7] Synthesis of β- and γ-Carbolinones via Pd-Catalyzed Direct Dehydrogenative Annulation (DDA) of Indole-carboxamides with Alkynes Using Air as the Oxidant
Shi, Zhuangzhi
Cui, Yuxin
Jiao, Ning
[J]. ORGANIC LETTERS, 2010, 12 (13) : 2908 - 2911
[8] Synthesis of Phenanthridinones via the Palladium- Catalyzed Annulation of Benzyne
Witkowski, Dominick C.
McDermott, Luca
Garg, Neil K.
[J]. ORGANIC SYNTHESES, 2022, 99 : 159 - +
[9] Experiment and Theory of Bimetallic Pd-Catalyzed α-Arylation and Annulation for Naphthalene Synthesis
Ence, Chloe C.
Martinez, Erin E.
Himes, Samuel R.
Nazari, S. Hadi
Moreno, Mariur Rodriguez
Matu, Manase F.
Larsen, Samantha G.
Gassaway, Kyle J.
Valdivia-Berroeta, Gabriel A.
Smith, Stacey J.
Ess, Daniel H.
Michaelis, David J.
[J]. ACS CATALYSIS, 2021, 11 (16) : 10394 - 10404
[10] A Pd-catalyzed optional approach for the synthesis of dibenzothiophenes
Song, Juan
Wu, Hao
Sun, Wei
Wang, Songjiang
Sun, Haisen
Xiao, Kang
Qian, Yan
Liu, Chao
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (12) : 2083 - 2087

← 1 2 3 4 5 →