Direct C-H Alkylation of Naphthoquinone with Acetone and 1,3-Dicarbonyl Compounds via Radical Cross Dehydrogenation Coupling

被引：0

作者：

Ou, Jiankang ^{[1
]}

Liu, Haoyu ^{[1
]}

Fang, Zeguo ^{[1
]}

Zhang, Qian ^{[1
]}

Li, Dong ^{[1
]}

机构：

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

来源：

CHEMISTRYSELECT | 2024年 / 9卷 / 28期

关键词：

Alkylation; Naphthoquinone; Acetone; 1,3-Dicarbonyl compounds; Cross dehydrogenation coupling; METAL-FREE; QUINONES; FUNCTIONALIZATION; ARYLATION; DERIVATIVES; ROUTE;

D O I：

10.1002/slct.202402061

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A direct C-H alkylation of naphthoquinones with acetone and 1,3-dicarbonyl compounds was developed to construct C-C bonds of alkyl-substituted naphthoquinone derivatives. It proceeded through an oxidative radical cross dehydrogenation coupling process under simple and mild conditions. This method provides a facile and efficient route for synthesis of functionalized naphthoquinones from readily available feedstocks. Construction of C-C bonds of alkyl-substituted naphthoquinones through C-H/C-H cross dehydrogenation coupling of naphthoquinones with acetone and 1,3-dicarbonyl compounds was developed. image

引用

页数：4

共 42 条

[11] Practical C-H Functionalization of Quinones with Boronic Acids
Fujiwara, Yuta
Domingo, Victoriano
Seiple, Ian B.
Gianatassio, Ryan
Del Bel, Matthew
Baran, Phil S.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (10) : 3292 - 3295
[12] Progress towards metal-free radical alkylations of quinones under mild conditions
Galloway, Jordan D.
Baxter, Ryan D.
[J]. TETRAHEDRON, 2019, 75 (46)
[13] Radical Benzylation of Quinones via C-H Abstraction
Galloway, Jordan D.
Mai, Duy N.
Baxter, Ryan D.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (18) : 12131 - 12137
[14] Silver-Catalyzed Minisci Reactions Using Selectfluor as a Mild Oxidant
Galloway, Jordan D.
Mai, Duy N.
Baxter, Ryan D.
[J]. ORGANIC LETTERS, 2017, 19 (21) : 5772 - 5775
[15] Quinone C-H Alkylations via Oxidative Radical Processes
Hamsath, Akil
Galloway, Jordan D.
Baxter, Ryan D.
[J]. SYNTHESIS-STUTTGART, 2018, 50 (15): : 2915 - 2923
[16] K2S2O8-mediated metal-free direct C-H functionalization of quinones using arylboronic acids
Ilangovan, Andivelu
Polu, Ashok
Satish, Gandhesiri
[J]. ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (12): : 1616 - 1620
[17] γ-Carbonyl Quinones: Radical Strategy for the Synthesis of Evelynin and Its Analogues by C-H Activation of Quinones Using Cyclopropanols
Ilangovan, Andivelu
Saravanakumar, Shanmugasundar
Malayappasamy, Subramani
[J]. ORGANIC LETTERS, 2013, 15 (19) : 4968 - 4971
[18] The recent advances in K2S2O8-mediated cyclization/coupling reactions via an oxidative transformation
Kumar, Sumit
Padala, Kishor
[J]. CHEMICAL COMMUNICATIONS, 2020, 56 (96) : 15101 - 15117
[19] LEOPOLD WR, 1984, CANCER RES, V44, P1928
[20] Quinones Derived from Plant Secondary Metabolites as Anti-cancer Agents
Lu, Jin-Jian
Bao, Jiao-Lin
Wu, Guo-Sheng
Xu, Wen-Shan
Huang, Ming-Qing
Chen, Xiu-Ping
Wang, Yi-Tao
[J]. ANTI-CANCER AGENTS IN MEDICINAL CHEMISTRY, 2013, 13 (03) : 456 - 463

← 1 2 3 4 5 →