Design, synthesis, and applications of stereospecific 1,3-diene carbonyls

被引：0

作者：

Qiang Feng ^{[1
]}

Shihui Wang ^{[1
]}

Xingxing Ma ^{[2
]}

Changqing Rao ^{[1
]}

Qiuling Song ^{[1
,2
,3
]}

机构：

[1] Institute of Next Generation Matter Transformation, College of Material Sciences & Engineering, Huaqiao University

[2] Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry, Fuzhou University

[3] School of Chemistry and Chemical Engineering, Henan Normal University

来源：

Science China(Chemistry) | 2022年 / 05期

关键词：

D O I：

暂无

中图分类号：

O621.3 [有机合成化学];

学科分类号：

070303 ; 081704 ;

摘要：

The strategy toward the synthesis of various 1,3-dienals or 1,3-dienones is disclosed between diazo compounds and furans,which features metal-free, additive-free, broad functional group tolerance, and readily accessible starting materials. Notably, this strategy is applicable in both intramolecular and intermolecular protocols. Mechanistic studies suggested that the reactions undergo a cyclopropanation/rearrangement sequence. With an E/E-1,3-dienal, corresponding N-tosylhydrazones were readily prepared and subjected to phenylboronic acid to form a double bond migration product and indoles to construct a five-member ring via [3 + 2] annulation reaction.

引用

页码：912 / 917

页数：6

共 23 条

[1]

The Cyclopropane Ring as a Reporter of Radical Leaving-Group Reactivity for Ni-Catalyzed C(sp<sup>3</sup>)-O Arylation.[J] Mills L Reginald;Monteith John J;Dos Passos Gomes Gabriel;Aspuru-Guzik Alán;Rousseaux Sophie A L Journal of the American Chemical Society 2020,

[2]

Nickel-Catalyzed Hydroarylation of in Situ Generated 1;3-Dienes with Arylboronic Acids Using a Secondary Homoallyl Carbonate as a Surrogate for the 1;3-Diene and Hydride Source.[J] Hamaguchi Takashi;Takahashi Yoshiyuki;Tsuji Hiroaki;Kawatsura Motoi Organic letters 2020,

[3]

Asymmetric catalysis in synthetic strategies for chiral benzothiazepines[J] Haifeng Wang;Shuangxi Gu;Qiongjiao Yan;Li Ding;Fen-Er Chen Green Synthesis and Catalysis 2020,

[4]

Overcoming Scope Limitations in Cross-Coupling of Diazo Nucleophiles by Manipulating Catalyst Speciation and Using Flow Diazo Generation[J] Ryan J. Sullivan;Garrett P. R. Freure;Stephen G. Newman ACS Catalysis 2019,

[5]

Modular and regioselective synthesis of all-carbon tetrasubstituted olefins enabled by an alkenyl Catellani reaction.[J] Wang Jianchun;Dong Zhe;Yang Cheng;Dong Guangbin Nature chemistry 2019,

[6]

Palladium-catalyzed synthesis of 3-trifluoromethylated 1;3-dienes from acrylate derivatives and BTP[J] Qun Zhao;Jianjun Wang;Tatiana Besset;Xavier Pannecoucke;Jean-Philippe Bouillon;Thomas Poisson Tetrahedron 2018,

[7]

Highly Stereoselective Synthesis of 1;3-Dienes through an Aryl to Vinyl 1;4-Palladium Migration/Heck Sequence.[J] Hu Tian-Jiao;Li Meng-Yao;Zhao Qian;Feng Chen-Guo;Lin Guo-Qiang Angewandte Chemie (International ed. in English) 2018,

[8]

Palladium-Catalyzed Synthesis of 3-Trifluoromethyl-Substituted 1;3-Butadienes by Means of Directed C-H Bond Functionalization.[J] Zhao Qun;Tognetti Vincent;Joubert Laurent;Besset Tatiana;Pannecoucke Xavier;Bouillon Jean-Philippe;Poisson Thomas Organic letters 2017,

[9]

Synthesis of 1;3-Dienes via a Sequential Suzuki-Miyaura Coupling/Palladium-Mediated Allene Isomerization Sequence.[J] Al-Jawaheri Yassir;Kimber Marc C Organic letters 2016,

[10]

Aminofluorination of Cyclopropanes: A Multifold Approach through a Common; Catalytically Generated Intermediate.[J] Pitts Cody Ross;Ling Bill;Snyder Joshua A;Bragg Arthur E;Lectka Thomas Journal of the American Chemical Society 2016,

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