Benzylation of heterocyclic N-oxides via direct oxidative cross-dehydrogenative coupling with toluene derivatives

被引：21

作者：

Wan, L. ^{[1
,2
]}

Qiao, K. ^{[1
]}

Sun, X. N. ^{[1
]}

Di, Z. C. ^{[1
]}

Fang, Z. ^{[1
]}

Li, Z. J. ^{[1
]}

Guo, K. ^{[1
,2
,3
]}

机构：

[1] Nanjing Tech Univ, Coll Biotechnol & Pharmaceut Engn, 30 Puzhu South Rd, Nanjing, Jiangsu, Peoples R China

[2] Jiangsu Natl Synerget Innovat Ctr Adv Mat SICAM, 30 Puzhu South Rd, Nanjing, Jiangsu, Peoples R China

[3] Nanjing Tech Univ, State Key Lab Mat Oriented Chem Engn, 5 Xinmofan Rd, Nanjing, Jiangsu, Peoples R China

来源：

NEW JOURNAL OF CHEMISTRY | 2016年 / 40卷 / 12期

基金：

中国国家自然科学基金;

关键词：

C-H BOND; HOMOLYTIC AROMATIC-SUBSTITUTION; CATALYZED DIRECT ARYLATION; CARBON-HYDROGEN BONDS; METAL-FREE; AMBIENT-TEMPERATURE; UNACTIVATED ARENES; DIRECT ALKYLATION; METHYL ARENES; O BOND;

D O I：

10.1039/c6nj02560a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel cross-dehydrogenative coupling (CDC) of heterocyclic N-oxides with toluene derivatives has been discussed, allowing for the facile synthesis of a broad range of structurally diverse C1-benzyl quinoline N-oxides, isoquinoline N-oxides and pyridine N-oxides, including two methylated quinoline N-oxides in particular. This protocol not only extends the application of toluenes in synthetic organic chemistry, but also offers an alternative method to prepare benzylated heterocyclic N-oxides without any metal involved, which is important in medicinal chemistry.

引用

页码：10227 / 10232

页数：6

共 50 条

[41] Tetrabutylammonium Iodide-Catalyzed Phosphorylation of Benzyl C-H Bonds via a Cross-Dehydrogenative Coupling (CDC) Reaction [J].

Xu, Jian ;

Zhang, Pengbo ;

Li, Xueqin ;

Gao, Yuzhen ;

Wu, Ju ;

Tang, Guo ;

Zhao, Yufen .

ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (16) :3331-3335

[42] Chiral organic contact ion pairs in metal-free catalytic enantioselective oxidative cross-dehydrogenative coupling of tertiary amines to ketones [J].

Zhang, Gen ;

Ma, Yunxia ;

Wang, Shoulei ;

Kong, Weidong ;

Wang, Rui .

CHEMICAL SCIENCE, 2013, 4 (06) :2645-2651

[43] Selective Cross-Dehydrogenative Coupling of Various Acyclic Enamides with Heteroarenes via Rh(III)-Catalyzed C-H Activation [J].

Li, Xiaolan ;

Luo, Haiqing ;

Song, Ruixin ;

Zhang, Yuting ;

Gong, Xian ;

Cai, Hu ;

Luo, Xuzhong .

ORGANIC LETTERS, 2023, 25 (28) :5262-5267

[44] Cross-dehydrogenative Coupling Reactions Between Formamidic C(sp2)-H and X-H (X = C, O, N) Bonds [J].

He, Zhe ;

Wu, Dan ;

Vessally, Esmail .

TOPICS IN CURRENT CHEMISTRY, 2020, 378 (06)

[45] C-H Arylation of Heterocyclic N-Oxides Through in Situ Diazotisation Of Anilines without Added Promoters: A Green And Selective Coupling Process [J].

Colleville, Aymeric P. ;

Horan, Richard A. J. ;

Olazabal, Sandrine ;

Tomkinson, Nicholas C. O. .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2016, 20 (07) :1283-1296

[46] Theoretical Investigations on Rh(III)-Catalyzed Cross-Dehydrogenative Aryl-Aryl Coupling via C-H Bond Activation [J].

Zhao, Dan ;

Li, Xiaoxi ;

Han, Keli ;

Li, Xingwei ;

Wang, Yong .

JOURNAL OF PHYSICAL CHEMISTRY A, 2015, 119 (12) :2989-2997

[47] Copper-Catalyzed Cross Dehydrogenative Coupling of N,N-Disubstituted Formamides and Phenols: A Direct Access to Carbamates [J].

Ali, Wajid ;

Rout, Saroj K. ;

Guin, Srimanta ;

Modi, Anju ;

Banerjee, Arghya ;

Patel, Bhisma K. .

ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (2-3) :515-522

[48] Cu-catalyzed one-pot synthesis of fused oxazepinone derivatives via sp2 C-H and O-H cross-dehydrogenative coupling [J].

Zhang, Zeyuan ;

Dai, Zhen ;

Ma, Xinkun ;

Liu, Yihan ;

Ma, Xiaojun ;

Li, Wanli ;

Ma, Chen .

ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (07) :799-803

[49] Organic photoredox catalyzed C(sp3)-H functionalization of saturated aza-heterocycles via a cross-dehydrogenative coupling reaction [J].

Zhang, Yi-Fan ;

Chen, Han-Nan ;

Xiao, Yi ;

Cui, Zhencun ;

Wang, Wei David ;

Xu, Guo-Qiang .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (41) :8284-8288

[50] Formation of C-O Bond via Cross-Dehydrogenative Coupling between Isochroman and Oxime under Metal-Free Oxidation Conditions [J].

He, Hua-Feng ;

Wang, Kai ;

Xing, Bo ;

Sheng, Guorong ;

Ma, Tingxuan ;

Bao, Weiliang .

SYNLETT, 2013, 24 (02) :211-214

← 1 2 3 4 5 →