Metal-Free Iodine-Catalyzed Oxidation of Ynamides and Diaryl Acetylenes into 1,2-Diketo Compounds

被引：41

作者：

Kim, Seung Woo

Um, Tae-Woong

Shin, Seunghoon ^{[1
]}

机构：

[1] Hanyang Univ, Ctr New Direct Organ Synth CNOS, Dept Chem, 222 Wangsimni Ro, Seoul 04763, South Korea

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 08期

基金：

新加坡国家研究基金会;

关键词：

EFFICIENT CATALYST; BENZIL DERIVATIVES; AEROBIC OXIDATION; MOLECULAR-IODINE; ALPHA-DIKETONES; ALKYNES; AZIRIDINATION; CYCLIZATION; OLEFINS; ALKENES;

D O I：

10.1021/acs.joc.8b00484

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Metal-free oxidation of ynamides is described, employing pyridine-N-oxides as oxidants under molecular iodine catalysis. In stark contrast to Bronsted acid catalysis, iodophilic activation of ynamides diverts the reaction manifold into a dioxygenation pathway. This oxidation is very rapid at room temperature with only 2.5 mol % I-2. Furthermore, this protocol could be extended to nonactivated alkynes, such as diarylacetylenes, to deliver various benzil derivatives.

引用

页码：4703 / 4711

页数：9

共 50 条

[1] Metal-free, iodine-catalyzed regioselective sulfenylation of indoles with thiols
Yi, Shanli
Li, Meichao
Mo, Weimin
Hu, Xinquan
Hu, Baoxiang
Sun, Nan
Jin, Liqun
Shen, Zhenlu
TETRAHEDRON LETTERS, 2016, 57 (17) : 1912 - 1916
[2] Metal-Free Iodine-Catalyzed Oxidative Dehydrogenation of N-Heterocycles
Li, Dengke
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 12 (04)
[3] Metal-Free Iodine-Catalyzed Direct Arylthiation of Substituted Anilines with Thiols
Yang, Daoshan
Yan, Kelu
Wei, Wei
Zhao, Jing
Zhang, Mengqi
Sheng, Xuguang
Li, Guoqing
Lu, Shenglei
Wang, Hua
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (12): : 6083 - 6092
[4] Metal-Free Iodine-Catalyzed Synthesis of Fully Substituted Pyrazoles and Its Sulphenylation
Sun, Jun
Qiu, Jiang-Kai
Zhu, Yi-Long
Guo, Cheng
Hao, Wen-Juan
Jiang, Bo
Tu, Shu-Jiang
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (16): : 8217 - 8224
[5] Facile Access to Benzothiophenes through Metal-Free Iodine-Catalyzed Intermolecular Cyclization of Thiophenols and Alkynes
Yana, Kelu
Yang, Daoshan
Zhang, Mengqi
Wei, Wei
Liu, Yao
Tian, Laijin
Wang, Hua
SYNLETT, 2015, 26 (13) : 1890 - 1894
[6] Metal-free synthesis of sulfonamides via iodine-catalyzed oxidative coupling of sulfonyl hydrazides and amines
Parumala, Santosh Kumar Reddy
Peddinti, Rama Krishna
TETRAHEDRON LETTERS, 2016, 57 (11) : 1232 - 1235
[7] Metal-free iodine-catalyzed direct cross-dehydrogenative coupling (CDC) between pyrazoles and thiols
Yang, Daoshan
Sun, Pengfei
Wei, Wei
Meng, Lingduan
He, Lingchao
Fang, Baokai
Jiang, Wei
Wang, Hua
ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (11): : 1457 - 1461
[8] Iodine-Catalyzed Amination of Benzoxazoles: A Metal-Free Route to 2-Aminobenzoxazoles under Mild Conditions
Lamani, Manjunath
Prabhu, Kandikere Ramaiah
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (19): : 7938 - 7944
[9] Iodine-catalyzed Sulfenylation of H-phosphonates with Diaryl Disulfides under Metal, Base and Solvent-free Conditions
Wu, Xiang-Mei
Hong, Yu-Xiang
LETTERS IN ORGANIC CHEMISTRY, 2017, 14 (01) : 49 - 55
[10] Iodine-Catalyzed Aza-Prins Cyclization: Metal-Free Synthesis and Antiproliferative Activity of Hexahydrobenzo[f]isoquinolines
Figueiredo, Carlos A. M.
Reddy, K. R. Kishore K.
Monteiro, Paula A.
de Carvalho, Joao E.
Ruiz, Ana L. T. G.
Silva, Luiz F., Jr.
SYNTHESIS-STUTTGART, 2013, 45 (08): : 1076 - 1082

← 1 2 3 4 5 →