- Transformations of N-arylpropiolamides to indoline-2,3-diones and acids via C≡C triple bond oxidative cleavage and C(sp2)–H functionalization
-
A new palladium-catalyzed oxidative conversion of N-arylpropiolamides and H2O to various indoline-2,3-diones and acids through the C≡C triple bond cleavage and C(sp2)–H functionalization is described, which is promoted by a cooperative action of catalytic CuBr2, 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) and O2. The method provides a practical tool for transformations of alkynes by means of a C–H functionalization strategy, which enables the formation of one C–C bond and multiple C–O bonds in a single reaction with high substrates compatibility and excellent functional group tolerance.
- Zhou, Ming-Bo,Li, Yang,Ouyang, Xuan-Hui,Li, Jin-Heng
-
p. 222 - 227
(2019/11/13)
-
- Facile synthesis of isatins by direct oxidation of indoles and 3-iodoindoles using NIS/IBX
-
A facile one-pot access to a broad range of isatins by direct oxidation of indoles using NIS/IBX reagent in DMSO at 25 °C in very good isolated yields is reported. It is shown by mechanistic investigations that a number of substituted indoles react rapidly with NIS in DMSO to produce intermediary 3-iodoindoles, which undergo oxidation subsequently to isatins with IBX.
- Chandra, Ajeet,Yadav, Navin R.,Moorthy, Jarugu Narasimha
-
supporting information
p. 2169 - 2174
(2019/03/04)
-
- Palladium-Catalyzed Oxidation of Indoles to Isatins by tert -Butyl Hydroperoxide
-
The combination of a Pd catalyst and tert -butyl hydroeroxide (TBHP) is a powerful catalytic system for many types of oxidative transformations. Here, we report that a Pd/TBHP system facilitates the oxidation of indoles with a range of functionalities to give the corresponding isatin derivatives in good yields.
- Luo, Junfei,Gao, Shanshan,Ma, Yaorui,Ge, Guoping
-
supporting information
p. 969 - 973
(2018/02/09)
-
- Cu-catalyzed oxidation of indoles to isatins
-
The first example of Cu-catalyzed oxidation of indoles to isatin derivatives by the use of cheap aqueous tert-butyl peroxide as an oxidant was developed. This methodology is practically convenient and highly functional group tolerant, allowing a variety of indole derivatives to transform into the corresponding isatin derivatives in good yields.
- Luo, Junfei,Zhao, Yanchao,Xu, Xing,Zheng, Junliang,Liang, Hongze
-
supporting information
p. 4591 - 4594
(2017/11/15)
-
- Visible Light Photocatalytic Aerobic Oxygenation of Indoles and pH as a Chemoselective Switch
-
An efficient chemodivergent strategy for visible light photocatalysis is developed. In the presence of a dicyanopyrazine-derived chromophore (DPZ) photocatalyst, aerobic photooxygenation of indoles could produce either isatins or formylformanilides in satisfactory yields by judiciously selecting inorganic salts or modulating the reaction pH. The current chemodivergent method is also effective with 2-substituted indoles, opening straightforward synthetic routes to valuable 2,2-disubstituted 3-oxindoles, formylformanilide derivatives, and benzoxazinones. Mechanistic investigations involving cyclic voltammetry studies further confirm that reaction pH influences the electrochemical properties of DPZ, thus affecting the oxidative pathway by which indoles are being transformed.
- Zhang, Chenhao,Li, Sanliang,Bure?, Filip,Lee, Richmond,Ye, Xinyi,Jiang, Zhiyong
-
p. 6853 - 6860
(2016/10/18)
-
- Synthesis of isatins by I2/TBHP mediated oxidation of indoles
-
An I2/TBHP mediated oxidation of commercially available indoles has been developed, which affords isatins in moderate to good yields.
- Zi, You,Cai, Zhong-Jian,Wang, Shun-Yi,Ji, Shun-Jun
-
supporting information
p. 3094 - 3097
(2014/06/23)
-