Pd-catalyzed assembly of phenanthridines from aryl ketone O-acetyloximes and arynes through C-H bond activation

被引：27

作者：

Tang, Chen-Yu

Wu, Xin-Yan

Sha, Feng ^{[1
]}

Zhang, Fei

Li, Hao

机构：

[1] E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 05期

基金：

中国国家自然科学基金; 中国博士后科学基金;

关键词：

Arynes; Palladium; C-H bond activation; Phenanthridines; Aryl ketone O-acetyloximes; INTERNAL ALKYNES; EFFICIENT SYNTHESIS; POLYSUBSTITUTED PYRIDINES; REGIOSELECTIVE SYNTHESIS; OXIDATIVE ANNULATION; TERMINAL ALKYNES; ISOQUINOLINES; INDOLES; DERIVATIVES; BENZYNE;

D O I：

10.1016/j.tetlet.2013.12.075

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pd-catalyzed annulation of aryne and aryl ketone O-acetyloxime via C-H bond activation was realized. Through the C-H bond activation/insertion/cyclization/elimination reaction sequence, phenanthridines are successfully constructed, providing an attractive strategy to approach substituted heterocycle without preactivation of starting materials. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.

引用

页码：1036 / 1039

页数：4

共 47 条

[1] Annulation of internal alkynes through a hydroamination/aza-Heck reaction sequence for the regioselective synthesis of indoles
Ackermann, Lutz
Sandmann, Rene
Villar, Amparo
Kaspar, Ludwig T.
[J]. TETRAHEDRON, 2008, 64 (05) : 769 - 777
[2] POTENTIAL ANTITUMOR AGENTS .55. 6-PHENYLPHENANTHRIDINE-4-CARBOXAMIDES - A NEW CLASS OF DNA-INTERCALATING ANTITUMOR AGENTS
ATWELL, GJ
BAGULEY, BC
DENNY, WA
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (04) : 774 - 779
[3] Recent advances in the transition metal-catalyzed twofold oxidative C-H bond activation strategy for C-C and C-N bond formation
Cho, Seung Hwan
Kim, Ji Young
Kwak, Jaesung
Chang, Sukbok
[J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) : 5068 - 5083
[4] Synthesis of dihydropyridines and pyridines from Imines and alkynes via C-H activation
Colby, Denise A.
Bergman, Robert G.
Ellman, Jonathan A.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (11) : 3645 - 3651
[5] Pd(II)-Catalyzed Synthesis of Carbolines by Iminoannulation of Internal Alkynes via Direct C-H Bond Cleavage Using Dioxygen as Oxidant
Ding, Shengtao
Shi, Zhuangzhi
Jiao, Ning
[J]. ORGANIC LETTERS, 2010, 12 (07) : 1540 - 1543
[6] Gandeepan P., 2013, ORG LETT, V15, P2804
[7] Palladium-Catalyzed Annulation of Acyloximes with Arynes (or Alkynes) Synthesis of Phenanthridines and Isoquinolines
Gerfaud, Thibaud
Neuville, Luc
Zhu, Jieping
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (03) : 572 - 577
[8] Rhodium(III)-Catalyzed Isoquinolone Synthesis: The N-O Bond as a Handle for C-N Bond Formation and Catalyst Turnover
Guimond, Nicolas
Gouliaras, Christina
Fagnou, Keith
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (20) : 6908 - +
[9] Isoquinoline Synthesis via Rhodium-Catalyzed Oxidative Cross-Coupling/Cyclization of Aryl Aldimines and Alkynes
Guimond, Nicolas
Fagnou, Keith
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (34) : 12050 - +
[10] Guitian E., 2005, TOPICS ORGANOMETALLI

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