Palladium-Catalyzed Double Decarboxylative [3+2] Annulation of Naphthalic Anhydrides with Internal Alkynes

被引：1

作者：

Kanganavaree, Chaipot ^{[1
]}

Kantarod, Kritchasorn ^{[1
]}

Worakul, Thanapat ^{[1
]}

Soorukram, Darunee ^{[1
,2
]}

Kuhakarn, Chutima ^{[1
,2
]}

Chakarawet, Khetpakorn ^{[1
]}

Wattanathana, Worawat ^{[3
]}

Surawatanawong, Panida ^{[1
,2
]}

Reutrakul, Vichai ^{[1
,2
]}

Leowanawat, Pawaret ^{[1
,2
]}

机构：

[1] Mahidol Univ, Fac Sci, Dept Chem, Bangkok 10400, Thailand

[2] Mahidol Univ, Fac Sci, Ctr Excellence Innovat Chem PERCH CIC, Bangkok 10400, Thailand

[3] Kasetsart Univ, Fac Engn, Dept Mat Engn, Bangkok 10900, Thailand

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 20期

关键词：

HYDROGEN-BOND PATTERNS; GRAPH-SET ANALYSIS; C-H; CARBOXYLIC-ACIDS; ACCESS; ACENAPHTHYLENES; DERIVATIVES; ACTIVATION; AZULENE; COPPER;

D O I：

10.1021/acs.joc.4c01747

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A palladium-catalyzed [3 + 2] annulation of naphthalic anhydrides with internal alkynes has been developed. The present protocol offers an efficient and convenient route to access a series of 1,2-disubstituted acenaphthylenes with excellent functional group compatibility. The reaction is proposed to proceed through a double decarboxylation sequence. The reported synthetic protocols can be extended to napthalene- and perylenedicarboximide-containing substrates. The molecular structures, photophysical properties, and frontier molecular orbitals of the obtained adducts were investigated by X-ray crystallography, UV-vis and fluorescence spectroscopy, and DFT calculations.

引用

页码：15083 / 15090

页数：8

共 57 条

[1] Synthesis of 1,2-Disubstituted Acenaphthylenes by Palladium-Catalyzed Annulation Reactions of Dibromoarenes with Internal Alkynes [J].

An, Wenbo ;

Li, Gaoqiang ;

Ma, Jun ;

Tian, Youping ;

Xu, Feng .

SYNLETT, 2014, 25 (11) :1585-1590

[2] Copper and silver benzoate and aryl complexes and their implications for oxidative decarboxylative coupling reactions [J].

Baur, Andreas ;

Bustin, Katelyn A. ;

Aguilera, Ellen ;

Petersen, Jeffrey L. ;

Hoover, Jessica M. .

ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (04) :519-524

[3]

Bernstein J., 1993, Acta Crystallogr. Sect. A: Found. Crystallogr., V49, pc164

[4] Contorted aromatics via a palladium-catalyzed cyclopentannulation strategy [J].

Bheemireddy, Sambasiva R. ;

Ubaldo, Pamela C. ;

Finke, Aaron D. ;

Wang, Lichang ;

Plunkett, Kyle N. .

JOURNAL OF MATERIALS CHEMISTRY C, 2016, 4 (18) :3963-3969

[5] Synthesis of Multisubstituted 1-Naphthoic Acids via Ru-Catalyzed C-H Activation and Double-Alkyne Annulation under Air [J].

Chen, Honghao ;

Ouyang, Lufeng ;

Liu, Jidan ;

Shi, Wen-Jing ;

Chen, Guoshu ;

Zheng, Liyao .

JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (20) :12755-12763

[6] Nucleus-independent chemical shifts (NICS) as an aromaticity criterion [J].

Chen, ZF ;

Wannere, CS ;

Corminboeuf, C ;

Puchta, R ;

Schleyer, PV .

CHEMICAL REVIEWS, 2005, 105 (10) :3842-3888

[7] Palladium-catalyzed naphthylation of acenaphthylene [J].

Dyker, Gerald ;

Merz, Klaus ;

Oppel, Iris M. ;

Muth, Enrico .

SYNLETT, 2007, (06) :897-900

[8] GRAPH-SET ANALYSIS OF HYDROGEN-BOND PATTERNS IN ORGANIC-CRYSTALS [J].

ETTER, MC ;

MACDONALD, JC ;

BERNSTEIN, J .

ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE CRYSTAL ENGINEERING AND MATERIALS, 1990, 46 :256-262

[9] Palladium-Catalyzed Pentannulation of Polycyclic Aromatic Hydrocarbons [J].

Eversloh, Christian Luetke ;

Avlasevich, Yuri ;

Li, Chen ;

Muellen, Klaus .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (45) :12756-12762

[10] Which NICS aromaticity index for planar π rings is best? [J].

Fallah-Bagher-Shaidaei, H ;

Wannere, CS ;

Corminboeuf, C ;

Puchta, R ;

Schleyer, PV .

ORGANIC LETTERS, 2006, 8 (05) :863-866

← 1 2 3 4 5 6 →