Chlorobenzene-driven palladium-catalysed lactonisation of benzoic acids

被引：1

作者：

Abe, Masahiro ^{[1
]}

Mizukami, Akiho ^{[1
]}

Yoshida, Emi ^{[1
]}

Kimachi, Tetsutaro ^{[1
]}

Inamoto, Kiyofumi ^{[1
]}

机构：

[1] Mukogawa Womens Univ, Sch Pharm & Pharmaceut Sci, 11-68,9-Bancho, Nishinomiya, Hyogo 6638179, Japan

来源：

RSC ADVANCES | 2024年 / 14卷 / 02期

基金：

日本学术振兴会;

关键词：

Catalysis; -; Oxidants; Palladium;

D O I：

10.1039/d3ra08176a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein, we developed a palladium-catalysed C-H cyclisation of benzoic acids in chlorobenzene without additional oxidants. The key to the success of these reactions is the use of chlorobenzene, which serves a dual role as a solvent and an oxidant, thus providing a simple and efficient method for synthesising phthalides. Herein, we developed a palladium-catalysed C-H cyclisation of benzoic acids in chlorobenzene without additional oxidants.

引用

收藏

页码：808 / 811

页数：4

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共 18 条

[1] An organic cation as a silver(I) analogue for the arylation of sp2 and sp3 C-H bonds with iodoarenes [J].

Arroniz, Carlos ;

Denis, J. Gabriel ;

Ironmonger, Alan ;

Rassias, Gerasimos ;

Larrosa, Igor .

CHEMICAL SCIENCE, 2014, 5 (09) :3509-3514

[2] Recent advancements in synthetic methodologies of 3-substituted phthalides and their application in the total synthesis of biologically active natural products [J].

Awasthi, Amardeep ;

Singh, Mandeep ;

Rathee, Garima ;

Chandra, Ramesh .

RSC ADVANCES, 2020, 10 (21) :12626-12652

[3] Palladium-catalyzed chemoselective direct α-arylation of carbonyl compounds with chloroaryl triflates at the C-Cl site [J].

Chen, Zicong ;

Gu, Changxue ;

Yuen, On Ying ;

So, Chau Ming .

CHEMICAL SCIENCE, 2022, 13 (17) :4762-4769

[4] Productive utilization of chlorobenzene: Palladium-catalyzed selective oxidation of alcohols [J].

Guram, AS ;

Bei, XH ;

Turner, HW .

ORGANIC LETTERS, 2003, 5 (14) :2485-2487

[5] Phthalides and Phthalans: Synthetic Methodologies and Their Applications in the Total Synthesis [J].

Karmakar, Raju ;

Pahari, Pallab ;

Mal, Dipakranjan .

CHEMICAL REVIEWS, 2014, 114 (12) :6213-6284

[6] Electrochemical C(sp3)-H Lactonization of 2-Alkylbenzoic Acids toward Phthalides [J].

Kwak, Jae-Hwan ;

Park, Yohan ;

Hong, Jee Eun ;

Yoon, Jisong ;

Baek, Woohyun ;

Kim, Kyumin .

ORGANIC LETTERS, 2023, 25 (01) :298-303

[7] Pt-catalyzed sp3 C-H bond activation of o-alkyl substituted aromatic carboxylic acid derivatives for the formation of aryl lactones [J].

Lee, JM ;

Chang, S .

TETRAHEDRON LETTERS, 2006, 47 (09) :1375-1379

[8] Visible Light-Promoted Magnesium, Iron, and Nickel Catalysis Enabling C(sp3)-H Lactonization of 2-Alkylbenzoic Acids [J].

Li, Sasa ;

Su, Mincong ;

Sun, Jie ;

Hu, Kunjun ;

Jin, Jian .

ORGANIC LETTERS, 2021, 23 (15) :5842-5847

[9] From Seeds of Apium graveolens Linn. to a Cerebral Ischemia Medicine: The Long Journey of 3-n-Butylphthalide [J].

Marco-Contelles, Jose ;

Zhang, Yihua .

JOURNAL OF MEDICINAL CHEMISTRY, 2020, 63 (21) :12485-12510

[10] Synergistic Palladium-Catalyzed C(sp3)?H Activation/C(sp3)?O Bond Formation: A Direct, Step-Economical Route to Benzolactones [J].

Novak, Petr ;

Correa, Arkaitz ;

Gallardo-Donaire, Joan ;

Martin, Ruben .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (51) :12236-12239