Palladium-Catalyzed Chemo- and Regiocontrolled Tandem Cyclization/Cross-Coupling of 2-Benzyl-3-alkynyl Chromones with Aryl Iodides for the Synthesis of 4H-Furo[3,2-c]chromenes and Xanthones

被引：2

作者：

Liang, Yi-En ^{[1
]}

Kan, Chih-Yu ^{[1
]}

Barve, Balaji D. ^{[1
]}

Chen, Yen-An ^{[1
]}

Li, Wen-Tai ^{[1
]}

机构：

[1] Minist Hlth & Welf, Natl Res Inst Chinese Med, Taipei 11221, Taiwan

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 37期

关键词：

HIGHLY SUBSTITUTED FURANS; METAL VINYLIDENES; ALKYNES; ARYLATION; SCAFFOLD; 3-(1-ALKYNYL)CHROMONES; CONSTRUCTION; GLYCOSIDES; ALCOHOLS;

D O I：

10.1021/acs.orglett.2c02476

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel Pd-catalyzed chemo-and regiocontrolled tandem cyclization/cross-coupling reaction of 3-alkynyl chromone with aryl iodide was developed for the synthesis of 4H-furo[3,2-c]chromenes and xanthones. The difunctionalization of alkynes through O-attack/5-exo-dig and C-attack/6-endo-dig cyclization was reported by this rare approach, which was selectively controlled by the addition of KF or a bidentate phosphine ligand. A one-pot tandem process was demonstrated directly from gamma-alkynyl-1,3-diketone for this method.

引用

页码：6728 / 6733

页数：6

共 73 条

[1] Xanthones from the botanical dietary supplement mangosteen (Garcinia mangostana) with aromatase inhibitory activity [J].

Balunas, Marcy J. ;

Su, Bin ;

Brueggemeier, Robert W. ;

Kinghorn, A. Douglas .

JOURNAL OF NATURAL PRODUCTS, 2008, 71 (07) :1161-1166

[2] Pd-Catalyzed and ligand-enabled alkene difunctionalization via unactivated C-H bond functionalization [J].

Barve, Balaji D. ;

Kuo, Yao-Haur ;

Li, Wen-Tai .

CHEMICAL COMMUNICATIONS, 2021, 57 (91) :12045-12057

[3] Stereodivergent Catalysis [J].

Beletskaya, Irina P. ;

Najera, Carmen ;

Yus, Miguel .

CHEMICAL REVIEWS, 2018, 118 (10) :5080-5200

[4] Metal vinylidenes and allenylidenes in catalysis: Applications in anti-Markovnikov additions to terminal alkynes and alkene metathesis [J].

Bruneau, C ;

Dixneuf, PH .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (14) :2176-2203

[5] Transition-Metal-Catalyzed Intramolecular Nucleophilic Addition of Carbonyl Groups to Alkynes [J].

Chen, Lianfen ;

Chen, Kai ;

Zhu, Shifa .

CHEM, 2018, 4 (06) :1208-1262

[6] One-pot synthesis of furocoumarins through cascade addition-cyclization-oxidation [J].

Cheng, Gang ;

Hu, Youhong .

CHEMICAL COMMUNICATIONS, 2007, (31) :3285-3287

[7] Divergent Gold Catalysis: Unlocking Molecular Diversity through Catalyst Control [J].

Chintawar, Chetan C. ;

Yadav, Amit K. ;

Kumar, Anil ;

Sancheti, Shashank P. ;

Patil, Nitin T. .

CHEMICAL REVIEWS, 2021, 121 (14) :8478-8558

[8] Palladium-Catalyzed Oxidative Carbocyclizations [J].

Deng, Youqian ;

Persson, Andreas K. A. ;

Backvall, Jan-E. .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (37) :11498-11523

[9] Neuroprotective Xanthone Glycosides from Swertia punicea [J].

Du, Xin-Gang ;

Wang, Wei ;

Zhang, Shi-Ping ;

Pu, Xiao-Ping ;

Zhang, Qing-Ying ;

Ye, Min ;

Zhao, Yu-Ying ;

Wang, Bao-Rong ;

Khan, Ikhlas A. ;

Guo, De-An .

JOURNAL OF NATURAL PRODUCTS, 2010, 73 (08) :1422-1426

[10] Synthesis of 2-substitued 3-aroylindenes via palladium-catalyzed carbonylative cyclization of diethyl 2-(2-(1-alkynyl)phenyl) malonates with aryl halides [J].

Duan, Xin-Hua ;

Guo, Li-Na ;

Bi, Hai-Peng ;

Liu, Xue-Yuan ;

Liang, Yong-Min .

ORGANIC LETTERS, 2006, 8 (14) :3053-3056

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