65109-80-0Relevant academic research and scientific papers
Gold(I)-Catalyzed Intramolecular Hydroarylation of Phenol-Derived Propiolates and Certain Related Ethers as a Route to Selectively Functionalized Coumarins and 2 H-Chromenes
Cervi, Aymeric,Vo, Yen,Chai, Christina L. L.,Banwell, Martin G.,Lan, Ping,Willis, Anthony C.
, p. 178 - 198 (2020/12/22)
Methods are reported for the efficient assembly of a series of phenol-derived propiolates, including the parent system 56, and their Au(I)-catalyzed cyclization (intramolecular hydroarylation) to give the corresponding coumarins (e.g., 1). Simple syntheses of natural products such as ayapin (144) and scoparone (145) have been realized by such means, and the first of these subject to single-crystal X-ray analysis. A related process is described for the conversion of propargyl ethers such as 156 into the isomeric 2H-chromene precocene I (159), a naturally occurring inhibitor of juvenile hormone biosynthesis.
Reductive cleavage of aryl O-carbamates to phenols by the Schwartz reagent. Expedient link to the directed ortho metalation strategy?
Morin, Justin,Zhao, Yigang,Snieckus, Victor
supporting information, p. 4102 - 4105 (2013/09/12)
A general, mild, and efficient method for the reductive cleavage of aryl O-carbamates to phenols, 1 → 2 using the Schwartz reagent is reported. The method is selective, tolerating a large number of functional groups; may be carried out by direct or by an economical in situ procedure; and, notably, establishes a synthetic connection to the directed ortho metalation strategy (Figure 1) allowing new entries into difficult to prepare contiguously substituted aromatics and heteroaromatics.
HF-Pyridine: A versatile promoter for monoacylation/sulfonylation of phenolic diols and for direct conversion of t-butyldimethylsilyl ethers to the corresponding acetates
Michigami, Kyosuke,Yoshimoto, Kazuya,Hayashi, Masahiko
scheme or table, p. 138 - 139 (2012/03/09)
Monoacylation and trifluoromethanesulfonylation of phenolic diols were achieved by the aid of HF-pyridine, whereas diacylation occurred with pyridine alone. Furthermore, HF-pyridine was found to promote the direct conversion of t-butyldimethylsilyl ethers to the corresponding acetates.
A Facile Preparation of Aryl Triflates. Decomposition of Arenediazonium Tetrafluoroborate Salts in Trifluoromethanesulfonic Acid
Yoneda, Norihiko,Fukuhara, Tsuyoshi,Mizokami, Takao,Suzuki, Akira
, p. 459 - 460 (2007/10/02)
The thermal or photochemical decomposition of arenediazonium tetrafluoroborate salts n trifluoromethanesulfonic acid, with or without organic bases such as pyridine, provides aryl triflates in high yields.
Acid-Catalyzed Solvolysis of N-Sulfonyl- and N-Acyl-O-arylhydroxylamines. Phenoxenium Ions
Endo, Yasuyuki,Shudo, Koichi,Okamoto, Toshihiko
, p. 6393 - 6397 (2007/10/02)
The acid-catalyzed reaction of N-acyl- and N-sulfonyl-O-arylhydroxylamines with benzene proceeded quite smoothly to give 2- and 4-hydroxybiphenyls.The results of product analysis, the orientation of the reaction, and the effects of substituents on the nitrogen atom and on the phenyl ring suggested a mechanism that involves a phenoxenium ion.The phenoxenium ion was trapped by benzene and other various nucleophiles.
