Photoredox Decarboxylative C(sp3)-N Coupling of α-Diazoacetates with Alkyl N-Hydroxyphthalimide Esters for Diversified Synthesis of Functionalized N-Alkyl Hydrazones

被引：45

作者：

Chan, Chun-Ming ^{[1
]}

Xing, Qi ^{[1
]}

Chow, Yip-Chi ^{[1
]}

Hung, Sing-Fung ^{[1
]}

Yu, Wing-Yiu ^{[1
]}

机构：

[1] Hong Kong Polytech Univ, State Key Lab Chem Biol & Drug Discovery, Dept Appl Biol & Chem Technol, Hung Hom,Kowloon, Hong Kong, Peoples R China

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 19期

关键词：

REDOX-ACTIVE ESTERS; DIAZO-COMPOUNDS; BIOLOGICAL-ACTIVITIES; VERSATILE SYNTHONS; ELECTRON-TRANSFER; 1,2,4-TRIAZOLES; N; N-DIALKYLHYDRAZONES; EQUIVALENTS; DIAZOESTERS;

D O I：

10.1021/acs.orglett.9b03020

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein we report a metal-free photocatalytic coupling reaction for the synthesis of structurally and functionally diverse N-alkyl hydrazones from alpha-diazoacetates and N-alkyl hydroxyphthalimide esters. By employing Rose Bengal as a photocatalyst with yellow LEDs irradiation, over 60 N-alkyl hydrazones were synthesized. Fluorescence quenching analysis and deuterium incorporation experiments reveal that Hantzsch ester serves as both an electron donor and proton source for the reaction. This strategy offers a simple retrosynthetic disconnection for conventionally inaccessible C(sp(3))-rich N-alkyl hydrazones.

引用

页码：8037 / 8043

页数：7

共 83 条

[1]

Ali, 2017, J PHYTOCHEMISTRY BIO, V1, P104

[2] NHC catalysed direct addition of HMF to diazo compounds: synthesis of acyl hydrazones with antitumor activity [J].

Antonio, Joao P. M. ;

Frade, Raquel F. M. ;

Santos, Fabio M. F. ;

Coelho, Jaime A. S. ;

Afonso, Carlos A. M. ;

Gois, Pedro M. P. ;

Trindade, Alexandre F. .

RSC ADVANCES, 2014, 4 (55) :29352-29356

[3] Unexpected Reactivity of Trifluoromethyl Diazomethane (CF3CHN2): Electrophilicity of the Terminal N-Atom [J].

Arkhipov, Anton V. ;

Arkhipov, Viatcheslav V. ;

Cossy, Janine ;

Kovtunenko, Volodymir O. ;

Mykhailiuk, Pavel K. .

ORGANIC LETTERS, 2016, 18 (14) :3406-3409

[4]

Balasubramanian M., 1994, HETEROCYCLES, V37, P1951

[5] Formaldehyde N,N-Dialkylhydrazones as Neutral Formyl Anion Equivalents in Iridium-Catalyzed Asymmetric Allylic Substitution [J].

Breitler, Simon ;

Carreira, Erick M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (16) :5296-5299

[6] Transition-Metal-Free, Visible-Light-Enabled Decarboxylative Borylation of Aryl N-Hydroxyphthalimide Esters [J].

Candish, Lisa ;

Teders, Michael ;

Glorius, Frank .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (22) :7440-7443

[7] Synthesis and Biological Evaluation of Hydrazone Derivatives as Antifungal Agents [J].

Casanova, Bruna B. ;

Muniz, Mauro N. ;

de Oliveira, Thayse ;

de Oliveira, Luis Flavio ;

Machado, Michel M. ;

Fuentefria, Alexandre M. ;

Gosmann, Grace ;

Gnoatto, Simone C. B. .

MOLECULES, 2015, 20 (05) :9229-9241

[8] Recent developments in photochemical reactions of diazo compounds [J].

Ciszewski, Lukasz W. ;

Rybicka-Jasinska, Katarzyna ;

Gryko, Dorota .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (03) :432-448

[9] Practical Ni-Catalyzed Aryl-Alkyl Cross-Coupling of Secondary Redox-Active Esters [J].

Cornella, Josep ;

Edwards, Jacob T. ;

Qin, Tian ;

Kawamura, Shuhei ;

Wang, Jie ;

Pan, Chung-Mao ;

Gianatassio, Ryan ;

Schmidt, Michael ;

Eastgate, Martin D. ;

Baran, Phil S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (07) :2174-2177

[10]

Crabtree R. H., 2010, CHEM REV, V110, P575

← 1 2 3 4 5 6 7 8 9 →