Mechanistic Studies into Visible Light-Driven Carboxylation of Aryl Halides/Triflates by the Combined Use of Palladium and Photoredox Catalysts

被引：12

作者：

Toriumi, Naoyuki ^{[1
]}

Shimomaki, Katsuya ^{[1
]}

Caner, Joaquim ^{[1
]}

Murata, Kei ^{[1
]}

Martin, Ruben ^{[2
,3
]}

Iwasawa, Nobuharu ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Chem, Meguro Ku, Tokyo 1528551, Japan

[2] Barcelona Inst Sci & Technol, Inst Chem Res Catalonia ICIQ, Av Paisos Catalans 16, Tarragona 43007, Spain

[3] Catalan Inst Res & Adv Studies ICREA, Passeig Lluis Companys 23, Barcelona 08010, Spain

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 2021年 / 94卷 / 07期

关键词：

Carboxylation; Photoredox; Palladium; UNACTIVATED ALKYL; CARBON-DIOXIDE; ELECTRON-TRANSFER; HALIDES; CO2; REDUCTION; COMPLEXES; CHLORIDES;

D O I：

10.1246/bcsj.20210151

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reaction mechanism of palladium-catalyzed visible light-driven carboxylation of aryl halides and triflates with a photoredox catalyst was examined in detail. Experimental and theoretical studies indicated that the active species for photoredox-catalyzed reduction was cationic ArPd(II)(+) species to generate nucleophilic ArPd(I) or its further reduced ArPd(0)(-) species, which reacted with CO2 to give carboxylic acids. Hydrodehalogenated compounds, main byproducts in this carboxylation, were thought to be generated by protonation of these reduced species.

引用

页码：1846 / 1853

页数：8

共 7 条

[1] Visible-Light-Driven Carboxylation of Aryl Halides by the Combined Use of Palladium and Photoredox Catalysts
Shimomaki, Katsuya
Murata, Kei
Martin, Ruben
Iwasawa, Nobuharu
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (28) : 9467 - 9470
[2] Palladium-Catalyzed Visible-Light-Driven Carboxylation of Aryl and Alkenyl Triflates by Using Photoredox Catalysts
Shimomaki, Katsuya
Nakajima, Tomoya
Caner, Joaquim
Toriumi, Naoyuki
Iwasawa, Nobuharu
ORGANIC LETTERS, 2019, 21 (12) : 4486 - 4489
[3] Carboxylation of Aryl Triflates with CO2 Merging Palladium and Visible-Light-Photoredox Catalysts
Bhunia, Samir Kumar
Das, Pritha
Nandi, Shantanu
Jana, Ranjan
ORGANIC LETTERS, 2019, 21 (12) : 4632 - 4637
[4] Visible light-driven borylation of aryl halides by a B12 derivative based on a dual photoredox strategy
Sasaki, Kaito
Shichijo, Keita
Fujitsuka, Mamoru
Shimakoshi, Hisashi
JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, 2023, 27 (07N10) : 1270 - 1277
[5] Construction of a visible light-driven hydrocarboxylation cycle of alkenes by the combined use of Rh(I) and photoredox catalysts
Murata, Kei
Numasawa, Nobutsugu
Shimomaki, Katsuya
Takaya, Jun
Iwasawa, Nobuharu
CHEMICAL COMMUNICATIONS, 2017, 53 (21) : 3098 - 3101
[6] Improved Conditions for the Visible-Light Driven Hydrocarboxylation by Rh(I) and Photoredox Dual Catalysts Based on the Mechanistic Analyses
Murata, Kei
Numasawa, Nobutsugu
Shimomaki, Katsuya
Takaya, Jun
Iwasawa, Nobuharu
FRONTIERS IN CHEMISTRY, 2019, 7
[7] Conjugated Polymers as Photoredox Catalysts: Visible-Light-Driven Reduction of Aryl Aldehydes by Poly(p-phenylene)
Zhang, Miao
Rouch, William D.
McCulla, Ryan D.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (31) : 6187 - 6196

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