Gold-Catalyzed syn-1,2-Difunctionalization of Ynamides via Nitrile Activation

被引：64

作者：

Vanjari, Rajeshwer ^{[1
]}

Dutta, Shubham ^{[1
]}

Gogoi, Manash P. ^{[1
]}

Gandon, Vincent ^{[2
,3
]}

Sahoo, Akhila K. ^{[1
]}

机构：

[1] Univ Hyderabad, Sch Chem, Hyderabad 500046, Telangana, India

[2] Univ Paris Saclay, Univ Paris Sud, ICMMO, CNRS,UMR 8182, Batiment 420, F-91405 Orsay, France

[3] Univ Paris Saclay, Ecole Polytech, LCM, CNRS,UMR 9168, Route Saclay, F-91128 Palaiseau, France

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 24期

关键词：

DUAL-ACTIVATION; RAPID ACCESS; CYCLIZATION; CYCLOISOMERIZATION; ALKYNES;

D O I：

10.1021/acs.orglett.8b03830

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Developed is an unprecedented Au(I)-catalyzed syn-1,2-difunctionalization of ynamides with 2-amino-benzonitriles via nitrile activation. The coupling between ynamides and 2-aminobenzonitriles is explicitly regioselective, providing a straightforward access to 2,4-diamino-substituted quinolines. Density functional theory (DFT) study provides insightful information and rationalizes the reaction pathway. It shows how the synergy between ynamide pi-activation and nitrile sigma-coordination by the Au(I) catalyst makes the cyclization viable.

引用

页码：8077 / 8081

页数：5

共 50 条

[21] Gold-catalyzed synthesis of N-heterocycles using ynamides as diazoequivalents
Jimena, Fernando Sanchez-Cantalejo
Dos Santos, Mickael
Davies, Paul W.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 246
[22] ORGN 423-Palladium-catalyzed 1,1-and 1,2-difunctionalization of alkenes
Kalyani, Dipannita
Sanford, Melanie S.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 234
[23] Generation of α-Imin Gold Carbenes through Gold-Catalyzed Intermolecular Reaction of Azides with Ynamides
Shu, Chao
Wang, Yong-Heng
Zhou, Bo
Li, Xin-Ling
Ping, Yi-Fan
Lu, Xin
Ye, Long-Wu
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (30) : 9567 - 9570
[24] Iron-Catalyzed Intermolecular 1,2-Difunctionalization of Styrenes and Conjugated Alkenes with Silanes and Nucleophiles
Yang, Yuan
Song, Ren-Jie
Ouyang, Xuan-Hui
Wang, Cheng-Yong
Li, Jin-Heng
Luo, Shenglian
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (27) : 7916 - 7919
[25] Gold-Catalyzed Cascade Cyclization of (Azido)ynamides: An Efficient Strategy for the Construction of Indoloquinolines
Tokimizu, Yusuke
Oishi, Shinya
Fujii, Nobutaka
Ohno, Hiroaki
ORGANIC LETTERS, 2014, 16 (11) : 3138 - 3141
[26] Synthesis of α,β-Unsaturated Amidines through Gold-Catalyzed Intermolecular Reaction of Azides with Ynamides
Ruan, Peng-Peng
Li, Hang-Hao
Liu, Xin
Zhang, Te
Zuo, Shao-Xuan
Zhu, Chunyin
Ye, Long-Wu
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (17): : 9119 - 9125
[27] Transition-Metal-Catalyzed Carbohalogenative 1,2-Difunctionalization of C-C Multiple Bonds
Bag, Debojyoti
Mahajan, Shivangani
Sawant, Sanghapal D.
ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (19) : 3948 - 3970
[28] Gold-Catalyzed 1,2-Diarylation of Alkenes
Chintawar, Chetan C.
Yadav, Amit K.
Patil, Nitin T.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (29) : 11808 - 11813
[29] Photoinduced Copper-Catalyzed 1,2-Difunctionalization of 1,3-Dienes with Aryl Diselenides
Guo, Shengkun
Shen, Xiaoyu
Chen, Xiaoyun
Yu, Huaguang
Han, Ying
Yan, Chaoguo
Shi, Yaocheng
Hou, Hong
Zhu, Shaoqun
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (22): : 15969 - 15974
[30] Gold-Catalyzed 1,2-Carboxyarylation of Alkenes
Nanda, Tanmayee
Das, Avishek
Bera, Prafulla
Patil, Nitin T.
ORGANIC LETTERS, 2025, 27 (09) : 2228 - 2234

← 1 2 3 4 5 →