Modular Domino Process toward Highly Functionalized Pyrroles via Pd-Catalyzed [4+1] Annulation under Mild Conditions

被引：39

作者：

Zuo, Linhong ^{[1
]}

Yang, Yulian ^{[1
]}

Guo, Wusheng ^{[1
]}

机构：

[1] Xi An Jiao Tong Univ, Frontier Inst Sci & Technol FIST, Xian 710045, Shaanxi, Peoples R China

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 06期

关键词：

D O I：

10.1021/acs.orglett.1c00148

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Pd-catalyzed decarboxylative approach for the modular synthesis of highly functionalized pyrroles is presented. This protocol utilizes readily available cyclic carbonates and amines as reaction partners and only generates CO2 and H2O as byproducts. This methodology could be operated at room temperature and open to air, thus serving as an ideal means for the derivatization of bioactive compounds. Mechanism investigations suggested that the stereoselective formation of the (Z)-configured gamma-amino ketone intermediate is crucial for the success of the reaction.

引用

页码：2013 / 2018

页数：6

共 29 条

[21] Facile synthesis of holey lamellar CuO via ultrasonic chemical etching toward highly efficient hydrogenation of 4-nitrophenol under mild conditions
Geng, Longlong
Lin, Zhihui
Li, Zhaojun
An, Su
Zhang, Xiuling
Liu, Zhongmin
Zhang, Shuai
Zhang, Yong-Zheng
Gao, Shuang
Han, Haixiang
JOURNAL OF SOLID STATE CHEMISTRY, 2020, 292
[22] Mild Conditions for Pd-Catalyzed Carboamination of N-Protected Hex-4-enylamines and 1-, 3-, and 4-Substituted Pent-4-enylamines. Scope, Limitations, and Mechanism of Pyrrolidine Formation
Bertrand, Myra Beaudoin
Neukom, Joshua D.
Wolfe, John P.
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (22): : 8851 - 8860
[23] InCl3 catalyzed domino route to 2H-chromene-2-ones via [4+2] annulation of 2-hydroxyarylaldehydes with α-oxoketene dithioacetal under solvent-free conditions
Verma, Rajiv Kumar
Verma, Girijesh Kumar
Shukla, Gaurav
Singh, Maya Shankar
RSC ADVANCES, 2012, 2 (06) : 2413 - 2421
[24] Rh(III)-Catalyzed Domino [4+2] Annulation/Aza-Michael Addition of N-(Pivaloyloxy)benzamides with 1,5-Enynes via C-H Activation: Synthesis of Functionalized Aromathecins
Reddy, Chada Raji
Mallesh, Kathe
Bodasu, Srinivas
Donthiri, Ramachandra Reddy
JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (12): : 7905 - 7915
[25] Chemo- and Regioselective Synthesis of Functionalized 1H-imidazo[1,5-a]indol-3(2H)-ones via a Redox-Neutral Rhodium(III)-Catalyzed [4+1] Annulation between Indoles and Alkynes
Zhao, Fei
Chen, Jing
Qiao, Jin
Lu, Yangbin
Zhang, Xiaoning
Mao, Hui
Lu, Shiyao
Gong, Xin
Liu, Siyu
Wu, Xiaowei
Dai, Long
ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (18) : 4380 - 4389
[26] Highly selective synthesis of 4(5)-aryl-, 2,4(5)-diaryl-, and 4,5-diaryl-1H-imidazoles via Pd-catalyzed direct C-5 arylation of 1-benzyl-1H-imidazole
Bellina, Fabio
Cauteruccio, Silvia
Di Fiore, Annarita
Marchetti, Chiara
Rossi, Renzo
TETRAHEDRON, 2008, 64 (26) : 6060 - 6072
[27] A [bmim]Cl-promoted domino protocol using an isocyanide-based [4+1]-cycloaddition reaction for the synthesis of diversely functionalized 3-alkylamino-2-alkyl/aryl/hetero-aryl indolizine-1-carbonitriles under solvent-free conditions
Atar, Amol Balu
Kang, Jongmin
Jadhav, Arvind H.
NEW JOURNAL OF CHEMISTRY, 2020, 44 (08) : 3241 - 3248
[28] FeF3-mediated tandem annulation: a highly efficient one-pot synthesis of functionalized N-methyl-3-nitro-4H-pyrimido [2, 1-b] [1, 3] benzothiazole-2-amine derivatives under neat conditions
Amol Balu Atar
Eunbi Han
Jongmin Kang
Molecular Diversity, 2020, 24 : 443 - 453
[29] FeF3-mediated tandem annulation: a highly efficient one-pot synthesis of functionalized N-methyl-3-nitro-4H-pyrimido [2, 1-b] [1,3] benzothiazole-2-amine derivatives under neat conditions
Atar, Amol Balu
Han, Eunbi
Kang, Jongmin
MOLECULAR DIVERSITY, 2020, 24 (02) : 443 - 453

← 1 2 3 →