2216-92-4Relevant articles and documents
Synthesis, isolation and characterization of cationic gold(I) N-heterocyclic carbene (NHC) complexes
De Fremont, Pierre,Stevens, Edwin D.,Fructos, Manuel R.,Mar Diaz-Requejo,Perez, Pedro J.,Nolan, Steven P.
, p. 2045 - 2047 (2006)
A number of cationic gold(I) complexes have been synthesized and found to be stabilized by the use of N-heterocyclic carbene ligands. These species are often employed as in situ-generated reactive intermediates in gold catalyzed organic transformations. An isolated, well-defined species was tested in gold-mediated carbene transfer reactions from ethyl diazoacetate. The Royal Society of Chemistry 2006.
Silver-prompted carbonitration of acrylamides for the synthesis of nitrating oxindoles
Wei, Xiao-Hong,Wu, Quan-Xiang,Yang, Shang-Dong
, p. 1417 - 1421 (2015)
A silver-prompted carbonitration of alkenes involving concomitant direct C-H functionalization and C-N bond formation to synthesize nitrating oxindoles has been developed. The CR TH2 receptor antagonist skeleton can be obtained from one of the products with further modification.
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Tien,Hunsberger
, p. 6696 (1955)
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Photoredox-Catalyzed α-Aminomethyl Carboxylation of Styrenes with Sodium Glycinates: Synthesis of γ-Amino Acids and γ-Lactams
Zhou, Cong,Li, Miao,Sun, Jianwei,Cheng, Jiang,Sun, Song
supporting information, p. 2895 - 2899 (2021/05/05)
A visible-light photoredox-catalyzed reductive α-aminomethyl carboxylation of styrenes with sodium glycinates and CO2 has been developed to synthesize a series of α,α-disubstituted γ-amino acids and γ-lactams with high efficiency and regioselectivity. Notably, CO2 released from the decarboxylation step can be reused for the subsequent carboxylation. Distinct from the previous reactions with the same type of substrates leading to simple decarboxylation and olefin hydroalkylation, this process involves additional CO2 sequestration, thus leading to olefin α-aminomethyl carboxylation. These findings not only provide new access to α,α-disubstituted γ-amino acids and γ-lactams but also serve as a proof of concept for CO2 reutilization in decarboxylation reactions.
Direct, Site-Selective and Redox-Neutral α-C?H Bond Functionalization of Tetrahydrofurans via Quantum Dots Photocatalysis
Chen, Bin,Ci, Rui-Nan,Huang, Cheng,Liu, Zan,Qiao, Jia,Song, Zi-Qi,Tung, Chen-Ho,Wu, Li-Zhu
supporting information, p. 27201 - 27205 (2021/11/16)
As one of the most ubiquitous bulk reagents available, the intrinsic chemical inertness of tetrahydrofuran (THF) makes direct and site-selective C(sp3)?H bond activation difficult, especially under redox neutral condition. Here, we demonstrate that semiconductor quantum dots (QDs) can activate α-C?H bond of THF via forming QDs/THF conjugates. Under visible light irradiation, the resultant alkoxyalkyl radical directly engages in radical cross-coupling with α-amino radical from amino C?H bonds or radical addition with alkene or phenylacetylene, respectively. In contrast to stoichiometric oxidant or hydrogen atom transfer reagents required in previous studies, the scalable benchtop approach can execute α-C?H bond activation of THF only by a QD photocatalyst under redox-neutral condition, thus providing a broad of value added chemicals starting from bulk THFs reagent.
Water-Involved Ring-Opening of 4-Phenyl-1,2,4-triazoline-3,5-dione for “Photo-Clicked” Access to Carbamoyl Formazan Photoswitches In Situ
Deng, Pengchi,Du, Guangxi,Jiang, Shichao,Shen, Xin,Su, Zhishan,Xie, Xinyu,Yu, Zhipeng,Zhang, Yan,Zhao, Xiaohu,Zheng, Yuanqin,Zhou, Yuqiao
supporting information, (2021/12/22)
Cyclic azodicarbonyl derivatives, particularly 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD), commonly serve as arenophile, dienophile, enophile and electrophile. Perplexed by its instability in aqueous environment, there are few studies focused on the transient intermediate produced by hydrolysis of PTAD to achieve synthetic significance. Herein, we describe a “photo-click” method that involves nitrile imine (NI) from diarylsydnone to capture the diazenecarbonyl-phenyl-carbamic acid (DACPA) generated by water-promoted ring-opening of PTAD. DFT calculation reveal that H-bonding interactions between PTAD and water are vital to form DACPA which exhibited an umpolung effect during ligation by nature bond orbit (NBO) analysis. The ultra-fast ligation resulted in carbamoyl formazans, as a unique Z?E photo-switchable linker on target molecules, including peptide and drugs, with excellent anti-fatigue performance. This strategy is showcased to construct highly functionalized carbamoyl formazans in situ for photo-pharmacology and material studies, which also expands the chemistry of PTAD in aqueous media.