84702-85-2Relevant academic research and scientific papers
Gold-Catalyzed Oxidation of Thioalkynes to Form Phenylthio Ketene Derivatives via a Noncarbene Route
Sharma, Pankaj,Singh, Rahulkumar Rajmani,Giri, Sovan Sundar,Chen, Liang-Yu,Cheng, Mu-Jeng,Liu, Rai-Shung
supporting information, p. 5475 - 5479 (2019/08/01)
Gold-catalyzed oxidations of thioalkynes with 8-methylquinoline oxides afford 2-phenylthioketenes that can be trapped efficiently with alcohols. The synthetic utility is manifested by terminal and internal thioalkynes over a wide scope, bearing esters, ke
Relative Rates of Metal-Free Azide-Alkyne Cycloadditions: Tunability over 3 Orders of Magnitude
Skelly, Patrick W.,Sae-Jew, Jirapon,Kitos Vasconcelos, Ana Paula,Tasnim, Jerin,Li, Longbo,Raskatov, Jevgenij A.,Braslau, Rebecca
, (2019/10/14)
The thermal (3 + 2) dipolar azide-alkyne cycloaddition, proceeding without copper or strained alkynes, is an underutilized ligation with potential applications in materials, bioorganic, and synthetic chemistry. Herein, we investigate the effects of alkyne substitution on the rate of this reaction, both experimentally and computationally. Electron-withdrawing groups accelerate the reaction, providing a range of relative rates from 1.0 to 2100 between the slowest and fastest alkynes studied. Unexpectedly, aryl groups conjugated to the alkyne significantly retard the reaction rate. In contrast, a sulfonyl, ester-substituted alkyne is reactive enough that it couples with an azide at room temperature in a few hours. This reactivity scale should provide a guide to those who wish to use this ligation under mild conditions.
Relative Rates of Metal-Free Azide-Alkyne Cycloadditions: Tunability over 3 Orders of Magnitude
Skelly, Patrick W.,Sae-Jew, Jirapon,Kitos Vasconcelos, Ana Paula,Tasnim, Jerin,Li, Longbo,Raskatov, Jevgenij A.,Braslau, Rebecca
, p. 13615 - 13623 (2019/11/14)
The thermal (3 + 2) dipolar azide-alkyne cycloaddition, proceeding without copper or strained alkynes, is an underutilized ligation with potential applications in materials, bioorganic, and synthetic chemistry. Herein, we investigate the effects of alkyne substitution on the rate of this reaction, both experimentally and computationally. Electron-withdrawing groups accelerate the reaction, providing a range of relative rates from 1.0 to 2100 between the slowest and fastest alkynes studied. Unexpectedly, aryl groups conjugated to the alkyne significantly retard the reaction rate. In contrast, a sulfonyl, ester-substituted alkyne is reactive enough that it couples with an azide at room temperature in a few hours. This reactivity scale should provide a guide to those who wish to use this ligation under mild conditions.
A heterogeneous copper(I)-catalyzed aerobic oxidative cross-dehydrogenative coupling of terminal alkynes with thiols leading to alkynyl sulfides
Fang, Zhiqiang,He, Wen,Cai, Mingzhong,Lin, Yang,Zhao, Hong
supporting information, p. 6463 - 6467 (2015/11/16)
A heterogeneous copper-catalyzed direct oxidative cross-dehydrogenative coupling of terminal alkynes with thiols was achieved in DMSO at 70 °C in the presence of an MCM-41-supported bidentate nitrogen copper(I) complex [MCM-41-2N-CuCl] and K2CO
Hypervalent iodine(iii)-induced oxidative [4+2] annulation of o-phenylenediamines and electron-deficient alkynes: Direct synthesis of quinoxalines from alkyne substrates under metal-free conditions
Okumura, Sota,Takeda, Youhei,Kiyokawa, Kensuke,Minakata, Satoshi
, p. 9266 - 9268 (2013/10/01)
Hypervalent iodine(iii)-induced oxidative [4+2] annulation of o-phenylenediamines and electron-deficient alkynes under metal-free conditions has been developed. The reaction allows for direct access to quinoxalines bearing two electron-withdrawing groups in an efficient manner.
Two Methoxycarbonylketen Equivalents as Dienophiles in the Diels-Alder Reaction
Gupta, Indranil,Yates, Peter
, p. 1227 - 1228 (2007/10/02)
Methyl methoxypropiolate and methyl (phenylthio)propiolate give Diels-Alder adducts with 1,3-dienes; the adducts with cyclopentadienes give methyl 3-oxobicyclohept-5-ene-2-carboxylates on hydrolysis.
