2170681-06-6Relevant articles and documents
Visible-light induced decarboxylative coupling of redox-active esters with disulfides to construct C-S bonds
Xiao, Zhiwei,Wang, Lu,Wei, Junjie,Ran, Chongzhao,Liang, Steven H.,Shang, Jingjie,Chen, Guang-Ying,Zheng, Chao
supporting information, p. 4164 - 4167 (2020/04/22)
A novel method has been established for the construction of C-S bonds using redox-active esters with disulfides in the presence of Ru-photoredox catalyst. This method exhibits remarkable functional group tolerance across a wide scope of substrates. Under
Photoredox Decarboxylative C(sp3)-N Coupling of α-Diazoacetates with Alkyl N-Hydroxyphthalimide Esters for Diversified Synthesis of Functionalized N-Alkyl Hydrazones
Chan, Chun-Ming,Xing, Qi,Chow, Yip-Chi,Hung, Sing-Fung,Yu, Wing-Yiu
supporting information, p. 8037 - 8043 (2019/10/11)
Herein we report a metal-free photocatalytic coupling reaction for the synthesis of structurally and functionally diverse N-alkyl hydrazones from α-diazoacetates and N-alkyl hydroxyphthalimide esters. By employing Rose Bengal as a photocatalyst with yellow LEDs irradiation, over 60 N-alkyl hydrazones were synthesized. Fluorescence quenching analysis and deuterium incorporation experiments reveal that Hantzsch ester serves as both an electron donor and proton source for the reaction. This strategy offers a simple retrosynthetic disconnection for conventionally inaccessible C(sp3)-rich N-alkyl hydrazones.
Photoredox-catalyzed decarboxylative alkylation/cyclization of alkynylphosphine oxides: a metal- and oxidant-free method for accessing benzo[b]phosphole oxides
Liu, Lixin,Dong, Jianyu,Yan, Yani,Yin, Shuang-Feng,Han, Li-Biao,Zhou, Yongbo
supporting information, p. 233 - 236 (2019/01/04)
By photoredox-catalysis, alkylation/aryl C-H cyclization of readily available alkynylphosphine oxides towards benzo[b]phospholes has been realized under metal- and oxidant-free conditions at room temperature. This reaction readily incorporates various functionalized alkyl groups into the benzo[b]phosphole skeletons, representing a mild and versatile tool for the preparation of valuable phosphole compounds.
Ru-Photoredox-Catalyzed Decarboxylative Oxygenation of Aliphatic Carboxylic Acids through N-(acyloxy)phthalimide
Zheng, Chao,Wang, Yuting,Xu, Yangrui,Chen, Zhen,Chen, Guangying,Liang, Steven H.
supporting information, p. 4824 - 4827 (2018/08/24)
Decarboxylative aminoxylation of aliphatic carboxylic acid derivatives with (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO) in the presence of ruthenium photoredox catalysis is reported. The key transformation entails a highly efficient photoredox catalytic cycle using Hantzsch ester as a reductant. The ensuing alkoxyamine can be readily converted to the corresponding alcohol in one pot, representing an alternative approach to access aliphatic alcohols under photoredox conditions.
A visible light-driven minisci-type reaction with N-hydroxyphthalimide esters
Kammer, Lisa Marie,Rahman, Aliyaah,Opatz, Till
, (2018/04/06)
A visible light-promoted protocol for the redox-neutral coupling of N-hydroxyphthalimide esters with different N-heterocyclic compounds is described. The reaction proceeds through an alkyl radical intermediate generated by reductive decarboxylation of N-hydroxyphthalimide esters. In contrast to the original Minisci protocol, polyalkylation can largely be avoided. Mechanistic investigations revealed a radical chain mechanism which in some cases can proceed even if no photocatalyst is added. This valuable and functional group-tolerant reaction produces substituted heterocycles in moderate to excellent yield. The use of inexpensive starting materials and LEDs as the light source are key features of this C–C bond formation.
Iron-Nitrate-Catalyzed Oxidative Esterification of Aldehydes and Alcohols with N-Hydroxyphthalimide: Efficient Synthesis of N-Hydroxyimide Esters
Xu, Xiaohe,Sun, Jian,Lin, Yuyan,Cheng, Jingya,Li, Pingping,Jiang, Xiaoying,Bai, Renren,Xie, Yuanyuan
supporting information, p. 7160 - 7166 (2017/12/28)
An Fe(NO3)3·9H2O-catalyzed cross-dehydrogenative coupling reaction between N-hydroxyphthalimide (NHPI) or N-hydroxysuccinimide (NHSI) and aldehydes or alcohols in air is described. This transformation represents an efficient approach to the preparation of N-hydroxyimide ester derivatives in moderate to excellent yields, and has a wide substrate scope.
