Palladium-Catalyzed Domino Process to Construct 2,3,9,9a-Tetrahydro-1H-Fluorene Derivatives:Transient σ-Alkylpalladium(II) Complex Mediated C(sp2)-H Bond Activation

被引：4

作者：

Chi, Xiaochen ^{[1
]}

Meng, Long ^{[1
]}

Pang, Qingyang ^{[1
]}

Guo, Lianfeng ^{[1
]}

Liu, Qing ^{[1
]}

Zhao, Pingping ^{[1
,2
]}

Zhang, Daopeng ^{[1
]}

Sun, Fenggang ^{[1
]}

Li, Xinjin ^{[1
]}

Liu, Hui ^{[1
]}

机构：

[1] Shandong Univ Technol, Sch Chem & Chem Engn, 266 West Xincun Rd, Zibo 255049, Peoples R China

[2] Shandong Univ Sci & Technol, Coll Chem & Environm Engn, 579 Qianwangang Rd, Qingdao 266590, Shandong, Peoples R China

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 8卷 / 12期

基金：

中国国家自然科学基金;

关键词：

transient complexes; palladium; domino reactions; C-H activation; 2; 3; 9; 9a-tetrahydro-1H-fluorene derivatives; NATURAL-PRODUCTS; DIRECT ARYLATION; H ACTIVATION; METAL; CYCLOISOMERIZATION; ALKYLATION;

D O I：

10.1002/ajoc.201900600

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A palladium-catalyzed cascade reaction involving domino Heck/intramolecular C-H arylation to construct 2,3,9,9a-tetrahydro-1H-fluorene derivatives was developed. Products are obtained in moderate to excellent yields. The transient sigma-alkylpalladium(II) complex is the key intermediate, which mediates the C(sp(2))-H bond activation via a six-metallacycle. According to a transient sigma-alkylpalladium(II) complex, the control experiment demonstrates that beta-H elimination is faster than C-H activation. The methodology shows high chemoselectivity and good functional group tolerance.

引用

页码：2201 / 2204

页数：4

共 58 条

[1] Nonanomerlc spiroketals in natural products: Structures, sources, and synthetic strategies [J].

Aho, JE ;

Pihko, PM ;

Rissa, TK .

CHEMICAL REVIEWS, 2005, 105 (12) :4406-4440

[2] Synthesis, DNA affinity, and Antiprotozoal activity of fused ring dicationic compounds and their prodrugs [J].

Arafa, RK ;

Brun, R ;

Wenzler, T ;

Tanious, FA ;

Wilson, WD ;

Stephens, CE ;

Boykin, DW .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (17) :5480-5488

[3] Transition Metal Catalyzed Cycloisomerizations of 1,n-Allenynes and -Allenenes [J].

Aubert, Corinne ;

Fensterbank, Louis ;

Garcia, Pierre ;

Malacria, Max ;

Simonneau, Antoine .

CHEMICAL REVIEWS, 2011, 111 (03) :1954-1993

[4] RELATIONSHIP BETWEEN ANTIHISTAMINE AND ANTIDEPRESSANT ACTIVITY IN HEXAHYDROINDENOPYRIDINES [J].

AUGSTEIN, J ;

LEEMING, PR ;

HAM, AL .

JOURNAL OF MEDICINAL CHEMISTRY, 1972, 15 (05) :466-&

[5] Exploitation of cyclopropane ring-cleavage reactions for the rapid assembly of tetracyclic frameworks related to gibberellins [J].

Banwell, Martin G. ;

Phillis, Andrew T. ;

Willis, Anthony C. .

ORGANIC LETTERS, 2006, 8 (23) :5341-5344

[6] A PALLADIUM-CATALYZED CASCADE CYCLIZATION FRIEDEL-CRAFTS ALKYLATION APPROACH TO ANGULARLY FUSED-RING SYSTEMS [J].

BROWN, D ;

GRIGG, R ;

SRIDHARAN, V ;

TAMBYRAJAH, V .

TETRAHEDRON LETTERS, 1995, 36 (44) :8137-8140

[7] Palladium-Catalyzed Cascade Arene/Alkyne Annulation: Synthesis of Fluorene-Benzoxazine Derivatives [J].

Cai, Zhong-Jian ;

Li, Fang-Hui ;

Wang, Shun-Yi ;

Ji, Shun-Jun .

ORGANIC LETTERS, 2016, 18 (19) :4810-4813

[8]

Cao B., 2014, [No title captured], Patent No. [WO US2010/0075994, 20100075994]

[9] 6,12-Diarylindeno[1,2-b]fluorenes: Syntheses, Photophysics, and Ambipolar OFETs [J].

Chase, Daniel T. ;

Fix, Aaron G. ;

Kang, Seok Ju ;

Rose, Bradley D. ;

Weber, Christopher D. ;

Zhong, Yu ;

Zakharov, Lev N. ;

Lonergan, Mark C. ;

Nuckolls, Colin ;

Haley, Michael M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (25) :10349-10352

[10] Synthesis of Benzocyclobutenes by Palladium-Catalyzed C-H Activation of Methyl Groups: Method and Mechanistic Study [J].

Chaumontet, Manon ;

Piccardi, Riccardo ;

Audic, Nicolas ;

Hitce, Julien ;

Peglion, Jean-Louis ;

Clot, Eric ;

Baudoin, Olivier .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (45) :15157-15166

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