Synthesis of Fluoren-9-ones via Pd-Catalyzed Annulation of 2-Iodobiphenyls with Vinylene Carbonate

被引：3

作者：

Li, Wenguang ^{[1
,2
]}

Yu, Yongqi ^{[1
]}

Yang, Jie ^{[1
]}

Fu, Kaifang ^{[1
]}

Zhang, Xu ^{[1
]}

Shi, Shukui ^{[1
]}

Li, Ting ^{[1
]}

机构：

[1] Nanyang Normal Univ, Coll Chem & Pharmaceut Engn, Drug Synth Engn Technol Res Ctr Henan Prov Photoel, Engn Technol Res Ctr Henan Prov Solar Catalysis, Nanyang 473061, Henan, Peoples R China

[2] Henan Tianguan Enterprise Grp Co Ltd, State Key Lab Motor Vehicle Biofuel Technol, Nanyang 473000, Henan, Peoples R China

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2024年 / 19卷 / 04期

关键词：

C-H activation; palladium catalysis; vinylene carbonate; carbon monoxide transfer; versatile synthon; C-H ACTIVATION; ONE-POT SYNTHESIS; BOND ACTIVATION; BUILDING-BLOCKS; ARYL HALIDES; FLUORENONES; DERIVATIVES; ARYLATION; TILORONE; ROUTE;

D O I：

10.1002/asia.202301040

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A palladium-catalyzed reaction for intermolecular selective C-H cyclocarbonylation of 2-iodobiphenyls is described. Intriguingly, the vinylene carbonate acts as a carbon monoxide transfer agent to enable the annulation reaction. Moreover, as a versatile synthon, fluoren-9-one can be transformed into a variety of functionalized organic molecules, such as [1,1'-biphenyl]-2-carboxylic acid, 1'H,3'H-spiro[fluorene-9,2'-perimidine] and N-tosylhydrazones.

引用

收藏

页数：6

相关论文

共 50 条

[41] Z-Selective Synthesis of γ,δ-Unsaturated Ketones via Pd-Catalyzed Ring Opening of 2-Alkylenecyclobutanones with Arylboronic Acids [J].

Zhou, Yao ;

Rao, Changqing ;

Song, Qiuling .

ORGANIC LETTERS, 2016, 18 (16) :4000-4003

[42] Synthesis of dihydropyrans via Pd-catalyzed cyclization of 2-allyl-1,3-dicarbonyl compounds and vinylic triflates or halides [J].

Cacchi, S ;

Fabrizi, G ;

Larock, RC ;

Pace, P ;

Reddy, V .

SYNLETT, 1998, (08) :888-+

[43] Synthesis of Ladder-Type 9,9'-Bifluorenylidene-Based Conjugated Oligomers via a Pd-Catalyzed Tandem Suzuki Coupling/Heck Cyclization Approach [J].

Zhu, Xiaoyan ;

Liu, Feng ;

Ba, Xinwu ;

Wu, Yonggang .

ORGANIC LETTERS, 2022, 24 (31) :5851-5854

[44] Synthesis of 2,4,5-Trisubstituted Oxazoles via Pd-Catalyzed C-H Addition to Nitriles/Cyclization Sequences [J].

Zhang, Di ;

Song, Hao ;

Cheng, Na ;

Liao, Wei-Wei .

ORGANIC LETTERS, 2019, 21 (08) :2745-2749

[45] Selective synthesis of 2,3-dihydroquinazolin-4(1H)-ones and their N1-substituted analogues via Pd(II)-catalyzed cascade annulation of o-aminobenzoic acids with CO, ammonium acetate and aldehydes [J].

Zhang, Xiaopeng ;

Pang, Qiuyang ;

Liu, Dan ;

Zhang, Guisheng .

TETRAHEDRON, 2024, 155

[46] Direct Synthesis of Benzo[c]carbazoles by Pd-Catalyzed C-H [4+2] Annulation of 3-Arylindoles with External 1,3-Dienes [J].

Gerardin, Baptiste ;

Traboulsi, Iman ;

Pal, Suman ;

Lebunetelle, Gabrielle ;

Ramondenc, Yvan ;

Hoarau, Christophe ;

Schneider, Cedric .

ORGANIC LETTERS, 2022, :8164-8169

[47] Synthesis of N-isoindolinonyl peptides via Pd-catalyzed C(sp2)-H olefination-activation and their conformational studies [J].

Gupta, Manish K. K. ;

Panda, Ankita ;

Panda, Subhasish ;

Sharma, Nagendra K. K. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (24) :5104-5116

[48] Practical Pd(TFA)2-Catalyzed Aerobic [4+1] Annulation for the Synthesis of Pyrroles via "One-Pot" Cascade Reactions [J].

Yu, Yang ;

Mang, Zhiguo ;

Yang, Wei ;

Li, Hao ;

Wang, Wei .

CATALYSTS, 2016, 6 (11)

[49] Expeditious synthesis of C2- or N4-aryl-1,4-benzothiazin-3-one via orthogonal Pd-catalyzed C-arylation and Cu-catalyzed N-arylation [J].

Huang, Wei-Sheng ;

Xu, Rongsong ;

Dodd, Rory ;

Shakespeare, William C. .

TETRAHEDRON LETTERS, 2014, 55 (02) :441-444

[50] Pd-Catalyzed Csp2-H Functionalization of Heteroarenes via Isocyanide Insertion: Concise Synthesis of Di-(Hetero)Aryl Ketones and Di-(Hetero)Aryl Alkylamines [J].

Sharma, Upendra K. ;

Sharma, Nandini ;

Xu, Jun ;

Song, Gonghua ;

van der Eycken, Erik V. .

CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (13) :4908-4912

← 1 2 3 4 5 →