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

[31] Synthesis and properties of π-extended fluoranthene derivatives from 1,2-diarylacenaphthylene derivatives [J].

Matsuura, Kazuma ;

Nishida, Jun-ichi ;

Ito, Takaaki ;

Yokota, Ruri ;

Kitamura, Chitoshi ;

Kawase, Takeshi .

TETRAHEDRON, 2019, 75 (02) :278-285

[32]

Muller P., 2006, CRYSTAL STRUCTURE RE

[33] Corannulene: a molecular bowl of carbon with multifaceted properties and diverse applications [J].

Nestoros, Eleni ;

Stuparu, Mihaiela C. .

CHEMICAL COMMUNICATIONS, 2018, 54 (50) :6503-6519

[34] Palladium(II)-Catalyzed Oxidative Decarboxylative [2+2+1] Annulation of Cinnamic Acids with Alkynes: Access to Polysubstituted Pentafulvenes [J].

Peng, Shiyong ;

Chen, Nuan ;

Zhang, Hong ;

He, Min ;

Li, Hongguang ;

Lang, Ming ;

Wang, Jian .

ORGANIC LETTERS, 2020, 22 (14) :5589-5593

[35] Synthesis of Diarylated Aromatic Hydrocarbons by Dehydroxylation of Diols Using the Titanium(IV) Chloride and Triethylamine Reagent System [J].

Periasamy, Mariappan ;

Beesu, Mallesh ;

Shanmugaraja, Masilamani .

SYNTHESIS-STUTTGART, 2013, 45 (20) :2913-2918

[36] Palladium (II)-Catalyzed Decarboxylative Cross-Dehydrogenative Coupling: Direct Synthesis of meta-Substituted Biaryls from Aromatic Acids [J].

Pu, Fan ;

Zhang, Lin-Yan ;

Liu, Zhong-Wen ;

Shi, Xian-Ying .

ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (14) :2644-2649

[37]

Pyykkö P, 2015, J PHYS CHEM A, V119, P2326, DOI [10.1021/jp5065819, 10.1021/jp50658191]

[38] Decarboxylative reactions with and without light - a comparison [J].

Schwarz, Johanna ;

Koenig, Burkhard .

GREEN CHEMISTRY, 2018, 20 (02) :323-361

[39] Base-Selective Five- versus Six-Membered Ring Annulation in Palladium-Catalyzed C-C Coupling Cascade Reactions: New Access to Electron-Poor Polycyclic Aromatic Dicarboximides [J].

Seifert, Sabine ;

Schmidt, David ;

Shoyama, Kazutaka ;

Wuerthner, Frank .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (26) :7595-7600

[40] Recent developments in decarboxylative C(aryl)-X bond formation from (hetero)aryl carboxylic acids [J].

Sharma, Ruchi ;

Yadav, M. Ramu .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (25) :5476-5500

← 1 2 3 4 5 6 →