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

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