22001-35-0Relevant academic research and scientific papers
Copper porphyrin-catalyzed C(sp2)—O bond construction via coupling phenols with formamides
Yang, Shuang,Chen, Xiao-Yan,Xiong, Ming-Feng,Zhang, Hao,Shi, Lei,Lin, Dong-Zi,Liu, Hai-Yang
, p. 1541 - 1548 (2021/04/21)
Copper porphyrin-catalyzed construction of C(sp2)—O bond via coupling formamides with phenols was achieved firstly. A broad range of substrates afforded various carbamates in moderate to good yields with good functional group tolerance at low catalyst loading. Intermolecular competing kinetic isotope effect experiment indicated that the generation of formamide radical is the rate-determining step of current cross-dehydrogenative coupling (CDC) reaction. The research extends the application of metalloporphyrin in CDC reaction.
N-HYDROXYFORMAMIDE COMPOUNDS AND COMPOSITIONS COMPRISING THEM FOR USE AS BMP1, TLL1 AND/OR TLL2 INHIBITORS
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Page/Page column 135, (2017/01/26)
Compounds of Formulas (I) and (II) and salts thereof; methods of making and using the same, including use for inhibiting BMP1, TLL1 and/or TLL2 and in treatment of diseases associated with BMP1, TLL1 and/or TLL2 activity.
Tandem buildup of complexity of aromatic molecules through multiple successive electrophile generation in one pot, controlled by varying the reaction temperature
Sumita, Akinari,Otani, Yuko,Ohwada, Tomohiko
supporting information, p. 1680 - 1693 (2016/02/09)
While some sequential electrophilic aromatic substitution reactions, known as tandem/domino/cascade reactions, have been reported for the construction of aromatic single skeletons, one of the most interesting and challenging possibilities remains the one-pot build-up of a complex aromatic molecule from multiple starting components, i.e., ultimately multi-component electrophilic aromatic substitution reactions. In this work, we show how tuning of the leaving group ability of phenolate derivatives from carbamates and esters provides a way to successively generate multiple unmasked electrophiles in a controlled manner in one pot, simply by varying the temperature. Here, we demonstrate the autonomous formation of up to three bonds in one pot and formation of two bonds arising from a three-component electrophilic aromatic substitution reaction. This result provides a proof-of-concept of our strategy applicable for the self-directed construction of complex aromatic structures from multiple simple molecules, which can be a potential avenue to realize multi-component electrophilic aromatic substitution reactions.
A copper metal-organic framework as an efficient and recyclable catalyst for the oxidative cross-dehydrogenative coupling of phenols and formamides
Phan, Nam T.S.,Nguyen, Tung T.,Vu, Phuong H. L.
, p. 3068 - 3077 (2013/10/21)
A crystalline porous metal-organic framework Cu2(BPDC)2(BPY) (BPDC=4,4'-biphenyldicarboxylate, BPY=4,4'-bipyridine) was synthesized and characterized by several techniques including XRD, SEM, TEM, thermogravimetric analysis, FTIR, atomic absorption spectrophotometry, hydrogen temperature-programmed reduction, and nitrogen physisorption measurements. The Cu2(BPDC)2(BPY) could be employed as a heterogeneous catalyst for the copper-catalyzed cross-dehydrogenative coupling reaction of DMF with 2-substituted phenols to form organic carbamates through CH activation under oxidative conditions. The Cu2(BPDC)2(BPY) offered higher catalytic activity than common copper salts such as Cu(OAc)2, CuCl, CuCl2, CuI, and Cu(NO3)2 as well as other Cu-MOFs such as Cu3(BTC)2, Cu(BDC), and Cu(BPDC). The Cu2(BPDC)2(BPY) catalyst could be facilely separated from the reaction mixture, could be recovered and reused several times without significant degradation in catalytic activity.
