Copper-catalyzed C(sp3)-H/N-H Cross Dehydrogenative Coupling Between Toluene Derivatives and Picolinamides

被引：1

作者：

Ji, Huihui ^{[1
]}

Zhan, Hongju ^{[2
]}

Chen, Shumin ^{[2
]}

Fang, Zeguo ^{[1
]}

Zhang, Qian ^{[1
]}

Li, Dong ^{[1
,2
]}

机构：

[1] Hubei Univ Technol, New Mat & Green Mfg Talent Intro & Innovat Demons, Sch Mat & Chem Engn, Wuhan 430068, Peoples R China

[2] Jingchu Univ Technol, Hubei Prov Key Lab Drug Synth & Optimizat, Jingmen 448000, Peoples R China

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 11卷 / 10期

关键词：

amidation; benzylic C-H bond; copper; cross dehydrogenative coupling; toluene; C-H AMINATION; BOND FORMATION; INTRAMOLECULAR AMINATION; BENZYLIC HYDROCARBONS; CARBOXYLIC-ACIDS; N-METHYLATION; SIMPLE ETHERS; AMIDATION; FUNCTIONALIZATION; AMIDES;

D O I：

10.1002/ajoc.202200454

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient C-N bond formation method through copper-catalyzed C(sp3)-H/N-H cross dehydrogenative coupling between toluene derivatives and picolinamides was developed. The N-H bond of picolinamides was activated by the direction of pyridyl group without influence of remote C-H bonds. The method was applicable to a broad range of substrates with good functional group compatibility, which provided a novel route to prepare N-benzyl tertiary amides from cheap and readily available starting materials.

引用

页数：5

共 50 条

[31] Iodine-Catalyzed Synthesis of Chiral 4-Imidazolidinones Using α-Amino Acid Derivatives via Dehydrogenative N-H/C(sp3)-H Coupling [J].

Kanyiva, Kyalo Stephen ;

Tane, Marina ;

Shibata, Takanori .

JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (20) :12773-12783

[32] Computational Studies on the Mechanism of the Copper-Catalyzed sp3-C-H Cross-Dehydrogenative Coupling Reaction [J].

Cheng, Gui-Juan ;

Song, Li-Juan ;

Yang, Yun-Fang ;

Zhang, Xinhao ;

Wiest, Olaf ;

Wu, Yun-Dong .

CHEMPLUSCHEM, 2013, 78 (09) :943-951

[33] An unprecedented tandem synthesis of fluorescent coumarin-fused pyrimidines via copper-catalyzed cross-dehydrogenative C(sp3)-N bond coupling [J].

Kumari, Santosh ;

Shakoor, S. M. Abdul ;

Khullar, Sadhika ;

Mandal, Sanjay K. ;

Sakhuja, Rajeev .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (17) :3220-3228

[34] Copper-Catalyzed C(sp2)-C(sp3) Cross-Dehydrogenative Coupling of Quinones with Cyclic Alkanes: One-Step Access to Parvaquone and its Analogs [J].

Baral, Ek Raj ;

Kim, Sung Hong ;

Lee, Yong Rok .

ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 5 (09) :1134-1141

[35] Pd(II)-catalyzed Chelation-assisted Cross Dehydrogenative Coupling between Unactivated C(sp3)-H Bonds in Aliphatic Amides and Benzylic C-H Bonds in Toluene Derivatives [J].

Kubo, Teruhiko ;

Aihara, Yoshinori ;

Chatani, Naoto .

CHEMISTRY LETTERS, 2015, 44 (10) :1365-1367

[36] Synthesis of N-Azolylindoles by Copper-Catalyzed C-H/N-H Coupling-Annulation Sequence of o-Alkynylanilines [J].

Oda, Yoshiro ;

Hirano, Koji ;

Satoh, Tetsuya ;

Miura, Masahiro .

ORGANIC LETTERS, 2012, 14 (02) :664-667

[37] Intermolecular Amination of UnactivatedC(sp3)-H Bonds with Cyclic Alkylamines: Formation of C(sp3)-N Bonds through Copper/Oxygen-Mediated C(sp3)-H/N-H Activation [J].

Gou, Quan ;

Yang, Yu-Wen ;

Liu, Zi-Ning ;

Qin, Jun .

CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (45) :16057-16061

[38] Visible-Light-Promoted Radical Cross-Dehydrogenative Coupling of C(sp3)-H/C(sp3)-H and C(sp3)-H/C(sp2)-H via Intermolecular HAT [J].

Xie, Xinpeng ;

Qiao, Kaikai ;

Shao, Bing-ru ;

Jiang, Wenfeng ;

Shi, Lei .

ORGANIC LETTERS, 2023, 25 (23) :4264-4269

[39] Copper-catalyzed benzylic oxidation of C(sp3)-H bonds [J].

Zhang, Bo ;

Zhu, Shou-Fei ;

Zhou, Qi-Lin .

TETRAHEDRON, 2013, 69 (08) :2033-2037

[40] Pyridine-enabled copper-promoted cross dehydrogenative coupling of C(sp2)-H and unactivated C(sp3)-H bonds [J].

Wu, Xuesong ;

Zhao, Yan ;

Ge, Haibo .

CHEMICAL SCIENCE, 2015, 6 (10) :5978-5983

← 1 2 3 4 5 →