- Copper-Catalyzed Ullmann-Type Coupling and Decarboxylation Cascade of Arylhalides with Malonates to Access α-Aryl Esters
-
We have developed a high-efficiency and practical Cu-catalyzed cross-coupling to directly construct versatile α-aryl-esters by utilizing readily available aryl bromides (or chlorides) and malonates. These gram-scale approaches occur with turnovers of up to 1560 and are smoothly conducted by the usage of a low catalyst loading, a new available ligand, and a green solvent. A variety of functional groups are tolerated, and the application occurs with α-aryl-esters to access nonsteroidal anti-inflammatory drugs (NSAIDs) on the gram scale.
- Cheng, Fei,Chen, Tao,Huang, Yin-Qiu,Li, Jia-Wei,Zhou, Chen,Xiao, Xiao,Chen, Fen-Er
-
supporting information
p. 115 - 120
(2022/01/04)
-
- Copper-Catalysed (Diacetoxyiodo)benzene-Promoted Aerobic Esterification Reaction: Synthesis of Oxamates from Acetoacetamides
-
A copper-catalysed (diacetoxyiodo)benzene-promoted aerobic esterification reaction of acetoacetamides was developed for the synthesis of oxamates, which are useful precursors in synthetic organic chemistry. This practical and mild synthetic approach proceeded at 25 °C under open-air conditions and afforded methyl 2-oxo-2-(phenylamino)acetates in good to excellent yields combined with C?C σ-bond cleavage and formal oxidative C?H bond functionalization. A mechanism is proposed. (Figure presented.).
- Zhang, Zhiguo,Gao, Xiaolong,Yu, Haifeng,Zhang, Guisheng,Liu, Jianming
-
supporting information
p. 3406 - 3411
(2018/07/31)
-
- Carbamoyl Radicals via Photoredox Decarboxylation of Oxamic Acids in Aqueous Media: Access to 3,4-Dihydroquinolin-2(1 H)-ones
-
The first visible-light-mediated photoredox oxidative approach for generating carbamoyl radicals from oxamic acids is disclosed. Reaction of the generated carbamoyl radicals with electron-deficient alkenes opens efficient access to 3,4-dihydroquinolin-2(1H)-ones under mild conditions through a sequence of intermolecular radical addition, cyclization, and aromatization. The process is compatible with a variety of oxamic acids and electron-deficient alkenes, and a wide variety of 3,4-dihydroquinolin-2(1H)-ones were prepared.
- Bai, Qi-Fan,Jin, Chengan,He, Jing-Yao,Feng, Gaofeng
-
supporting information
p. 2172 - 2175
(2018/04/30)
-
- Metal-Free Oxidative C=C Bond Cleavage of Electron-Deficient Enamines Promoted by tert -Butyl Hydroperoxide
-
A novel tert -butyl hydroperoxide (TBHP)-promoted oxidative C=C double-bond cleavage of enamines is described. Heating a solution of an electron-deficient enamine in chlorobenzene at 80 °C in the presence of TBHP for two hours led to cleavage of the C=C bond. This study offers a new strategy to carry out C=O double-bond formation by the use of TBHP.
- Adib, Mehdi,Pashazadeh, Rahim,Gohari, Seyed Jamal Adin,Shahsavari, Fatemeh
-
supporting information
p. 1481 - 1485
(2017/08/15)
-
- Photoinduced Alcoholysis of Trihaloacetyl Group
-
Photolysis of trichloroacetamide in nondegassed methanol gave methyl oxanilate (13-44percent), along with carbamate (3-20percent) and amine (4-12percent).Similar irradiation of other trichloroacetylderivatives of aliphatic ketone, aldehyde, and acetate afforded only radical product.The results are interpreted in terms of the mechanism involving electron transfer of the radical pair.
- Izawa, Yasuji,Ishiguro, Katsuhiro,Tomioka, Hideo
-
p. 951 - 952
(2007/10/02)
-