Rhodium-Catalyzed Cascade Annulative Coupling of 3,5-Diarylisoxazoles with Alkynes

被引：9

作者：

Noguchi, Teppei ^{[1
]}

Nishii, Yuji ^{[2
]}

Miura, Masahiro ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan

[2] Osaka Univ, Grad Sch Engn, Frontier Res Base Global Young Researchers, Suita, Osaka 5650871, Japan

来源：

SYNTHESIS-STUTTGART | 2019年 / 51卷 / 01期

关键词：

C-H activation; annulative coupling; isoquinoline; rhodium catalyst; polyaromatic compounds; C-H ACTIVATION; ONE-POT SYNTHESIS; N BOND FORMATION; OXIDATIVE ANNULATION; RHODIUM(III)-CATALYZED SYNTHESIS; SEQUENTIAL CLEAVAGE; REGIOSELECTIVE SYNTHESIS; INTERNAL ALKYNES; DERIVATIVES; FUNCTIONALIZATION;

D O I：

10.1055/s-0037-1610376

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A rhodium-catalyzed cascade annulative coupling of 3,5-diarylisoxazoles with three equivalents of an alkyne proceeds smoothly in the presence of a Cu(II) oxidant, where the sequential construction of isoquinoline and naphtho[1,8-bc] pyran frameworks connected by a biaryl linkage is achieved by a single operation. Most of the obtained polycyclic compounds exhibit visible fluorescence in both the solution and the solid state. The hexaphenylated isoquinoline-naphthopyran conjugate (R = Ph) as a representative product shows a green emission which can be turned off by making an isoquinolinium salt with an acid. The emission is also reversibly turned on by treatment with a base.

引用

页码：258 / 270

页数：13

共 77 条

[1] Palladium-Catalyzed Selective Aryl Ring C-H Activation of N-Acyl-2-aminobiaryls: Efficient Access to Multiaryl-Substituted Naphthalenes
Annamalai, Pratheepkumar
Chen, Wu-Yin
Raju, Selvam
Hsu, Kou-Chi
Upadhyay, Nitinkumar Satyadev
Cheng, Chien-Hong
Chuang, Shih-Ching
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (22) : 3642 - 3648
[2] The larger acenes: Versatile organic semiconductors
Anthony, John E.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (03) : 452 - 483
[3] Remarkable Ability of the Benzylidene Ligand To Control Initiation of Hoveyda-Grubbs Metathesis Catalysts
Basak, Tymoteusz
Grudzien, Krzysztof
Barbasiewicz, Michal
[J]. EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2016, (21) : 3513 - 3523
[4] Alkenylation of Arenes and Heteroarenes with Alkynes
Boyarskiy, Vadim P.
Ryabukhin, Dmitry S.
Bokach, Nadezhda A.
Vasilyev, Aleksander V.
[J]. CHEMICAL REVIEWS, 2016, 116 (10) : 5894 - 5986
[5] Chelation-Assisted Nickel-Catalyzed Oxidative Annulation via Double C-H Activation/Alkyne Insertion Reaction
Castro, Luis C. Misal
Obata, Atsushi
Aihara, Yoshinori
Chatani, Naoto
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (04) : 1362 - 1367
[6] Cu-Rh Redox Relay Catalysts for Synthesis of Azaheterocycles via C-H Functionalization
Chiba, Shunsuke
[J]. CHEMISTRY LETTERS, 2012, 41 (12) : 1554 - 1559
[7] Heterocycle-Heterocycle Strategies: (2-Nitrophenyl)isoxazole Precursors to 4-Aminoquinolines, 1H-Indoles, and Quinolin-4(1H)-ones
Coffman, Keith C.
Palazzo, Teresa A.
Hartley, Timothy P.
Fettinger, James C.
Tantillo, Dean J.
Kurth, Mark J.
[J]. ORGANIC LETTERS, 2013, 15 (08) : 2062 - 2065
[8] Zincocenes as Mild Cyclopentadienyl Transfer Reagents toward Rhodium(I) Olefin Precursors. Facile Synthesis of (η5-Cp′)Rh(olefin)2 Compounds
Cristina Esqueda, Ana
Conejero, Salvador
Maya, Celia
Carmona, Ernesto
[J]. ORGANOMETALLICS, 2009, 28 (01) : 45 - 47
[9] Selective Cyclization of Arylnitrones to Indolines under External Oxidant-Free Conditions: Dual Role of Rh(III) Catalyst in the C-H Activation and Oxygen Atom Transfer
Dateer, Ramesh B.
Chang, Sukbok
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (15) : 4908 - 4911
[10] A facile access to substituted cationic 12-azapyrene salts by rhodium(III)-catalyzed C-H annulation of N-arylpyridinium salts
Feng, Boya
Wan, Danyang
Yan, Lipeng
Kadam, Vilas D.
You, Jingsong
Gao, Ge
[J]. RSC ADVANCES, 2016, 6 (71): : 66407 - 66411

← 1 2 3 4 5 6 7 8 →