33696-06-9Relevant academic research and scientific papers
Metal-Free Selective Modification of Secondary Amides: Application in Late-Stage Diversification of Peptides
Adebomi, Victor,Sriram, Mahesh,Streety, Xavier,Raj, Monika
supporting information, p. 6189 - 6193 (2021/08/01)
Here we solve a long-standing challenge of the site-selective modification of secondary amides and present a simple two-step, metal-free approach to selectively modify a particular secondary amide in molecules containing multiple primary and secondary amides. Density functional theory (DFT) provides insight into the activation of C-N bonds. This study encompasses distinct chemical advances for late-stage modification of peptides thus harnessing the amides for the incorporation of various functional groups into natural and synthetic molecules.
A specific and selective chemiluminescent probe for Pd2+ detection
Gao, Yuqi,Lin, Yuxing,Liu, Tingting,Zhang, Xiaomeng,Xu, Feng,Liu, Pan,Du, Lupei,Li, Minyong
supporting information, p. 63 - 66 (2018/04/05)
As an important transition metal catalyst, palladium is extensively used in many areas including electronics industry, petroleum industry, automobile industry and fine chemicals engineering. However, it brings harm to the environment as well as people's h
Transition-Metal-Free Esterification of Amides via Selective N-C Cleavage under Mild Conditions
Li, Guangchen,Lei, Peng,Szostak, Michal
supporting information, p. 5622 - 5625 (2018/09/25)
A general, transition-metal-free, and operationally simple method for esterification of amides by a highly selective cleavage of N-C(O) bonds under exceedingly mild conditions is reported. The reaction is characterized by broad substrate scope and excellent functional group tolerance. The potential of this mild esterification is highlighted by late-stage diversification of natural products and pharmaceuticals. Conceptually, the metal-free acyl functionalization of amides represents a significant step forward as a practical alternative to ligand exchange in acylmetal intermediates.
A chemiluminescence sensor with signal amplification based on a self-immolative reaction for the detection of fluoride ion at low concentrations
Hisamatsu, Shugo,Suzuki, Shinichi,Kohmoto, Shigeo,Kishikawa, Keiki,Yamamoto, Yusuke,Motokawa, Ryuhei,Yaita, Tsuyoshi
, p. 3993 - 3998 (2017/06/13)
A sensory system incorporated with an amplification function was developed for the detection of trace-level fluoride ions. This sensory system comprises two steps: amplification and chemiluminescence. These steps were linked with chemical reactions and we
A sensitive and selective chemiluminogenic probe for palladium
Turan, Ilke Simsek,Yilmaz, Ozge,Karatas, Betul,Akkaya, Engin U.
, p. 34535 - 34540 (2015/05/04)
Palladium triggered removal of a propargyl group leads to the cleavage of the 1,2-dioxetane ring, leading to bright chemiluminescence. The reaction of the probe is highly specific for the Pd species, thus the probe described here has considerable potentia
Metal-free synthesis of aryl esters by coupling aryl carboxylic acids and aryl boronic acids
Ruso, Jayaraman Sembian,Rajendiran, Nagappan,Kumaran, Rajendran Senthil
supporting information, p. 2345 - 2347 (2014/05/06)
A facile synthesis of aryl esters is developed by coupling aryl carboxylic acids and aryl boronic acids in the presence of PhI(OAc)2 and carbonyl diimidazole. A wide range of functional groups were tolerant to the metal-free reaction condition that led to the desired products in good yields.
Chemiluminescence sensing of fluoride ions using a self-immolative amplifier
Turan, Ilke Simsek,Akkaya, Engin U.
supporting information, p. 1680 - 1683 (2014/04/17)
An enhanced chemiluminescence signal is obtained when electronically triggered dioxetane cleavage is initiated by fluoride-mediated deprotection of the silyl-protecting group, followed by self-immolation via 1,4-quinone-methide rearrangement. The reaction
Synthesis, cytotoxicity and topoisomerase inhibition properties of multifarious aminoalkylated indeno[1,2-c]isoquinolin-5,11-diones
Ahn, Gang,Schifano-Faux, Nadège,Goossens, Jean-Fran?ois,Baldeyrou, Brigitte,Couture, Axel,Grandclaudon, Pierre,Lansiaux, Amélie,Ryckebusch, Adina
scheme or table, p. 2259 - 2263 (2011/05/15)
A number of mono- or diaminoalkylated indeno[1,2-c]isoquinolin-5,11-diones analogs of 1 were synthesized and evaluated for their DNA binding affinities, topoisomerase inhibition properties and antiproliferative activities against human cancer cell lines (
Kinetics and mechanism of nucleophilic displacement reactions of Y-substituted phenyl benzoates with cyanide Ion
Kim, Song-I,Kim, Eun-Hee,Um, Ik-Hwan
experimental part, p. 689 - 693 (2010/08/19)
Second-order rate constants (kCN-) have been measured for nucleophilic substitution reactions of Y-substituted phenyl benzoates (1a-r) with CN- ion in 80 mol % H2O/20 mol % DMSO at 25.0 ± 0.1 °C. The Bronsted-type plot is linear with βlg = -0.49, a typical βlg value for reactions reported to proceed through a concerted mechanism. Hammett plots correlated with σo and σ-constants exhibit many scattered points. In contrast, the Yukawa-Tsuno plot for the same reaction exhibits excellent linearity with pY = 1.37 and r = 0.34, indicating that a negative charge develops partially on the oxygen atom of the leaving aryloxide in the rate-determining step (RDS). Although two different mechanisms are plausible (i.e., a concerted mechanism and a stepwise pathway in which expulsion of the leaving group occurs at the RDS), the reaction has been concluded to proceed through a concerted mechanism on the basis of the magnitude of βlg and pY values.
Aminolysis of 2,4-dinitrophenyl X-substituted benzoates and Y-substituted phenyl benzoates in MeCN: Effect of the reaction medium on rate and mechanism
Um, Ik-Hwan,Jeon, Sang-Eun,Seok, Jin-Ah
, p. 1237 - 1243 (2008/09/18)
Second-order rate constants (kN) have been determined spectrophotometrically for the reactions of 2,4-di-nitrophenyl X-substituted benzoates (1a-f) and Y-substituted phenyl benzoates (2a-h) with a series of alicyclic secondary amines in MeCN at
