88358-25-2Relevant articles and documents
Photocatalyzed Triplet Sensitization of Oximes Using Visible Light Provides a Route to Nonclassical Beckmann Rearrangement Products
Zhang, Xiao,Rovis, Tomislav
, p. 21211 - 21217 (2021/12/27)
Oximes are valuable synthetic intermediates for the preparation of a variety of functional groups. To date, the stereoselective synthesis of oximes remains a major challenge, as most current synthetic methods either provide mixtures of E and Z isomers or furnish the thermodynamically preferred E isomer. Herein we report a mild and general method to achieve Z isomers of aryl oximes by photoisomerization of oximes via visible-light-mediated energy transfer (EnT) catalysis. Facile access to (Z)-oximes provides opportunities to achieve regio- and chemoselectivity complementary to those of widely used transformations employing oxime starting materials. We show an enhanced one-pot protocol for photocatalyzed oxime isomerization and subsequent Beckmann rearrangement that enables novel reactivity with alkyl groups migrating preferentially over aryl groups, reversing the regioselectivity of the traditional Beckmann reaction. Chemodivergent N- or O- cyclizations of alkenyl oximes are also demonstrated, leading to nitrones or cyclic oxime ethers, respectively.
Selective formation of secondary amides via the copper-catalyzed cross-coupling of alkylboronic acids with primary amides
Rossi, Steven A.,Shimkin, Kirk W.,Xu, Qun,Mori-Quiroz, Luis M.,Watson, Donald A.
supporting information, p. 2314 - 2317 (2013/06/05)
For the first time, a general catalytic procedure for the cross-coupling of primary amides and alkylboronic acids is demonstrated. The key to the success of this reaction was the identification of a mild base (NaOSiMe3) and oxidant (di-tert-butyl peroxide) to promote the copper-catalyzed reaction in high yield. This transformation provides a facile, high-yielding method for the monoalkylation of amides.
Potential Central Nervous System Active Agents. 4. Synthesis of N-Isobutylbenzamides
Agwada, Vincent C.,Beak, Peter
, p. 235 - 237 (2007/10/02)
The preparation and spectral properties (IR, 1HNMR) are given for 11 N-isobutylbenzamides, variously substituted on the acyl part with halo, methoxyl, methyl, or nitro groups, including two new ones.The amides were synthesized by the Schotten-Baumann meth
p-Fluorobenzoyl Chloride for Characterization of Active Hydrogen Functional Groups by Fluorine-19 Nuclear Magnetic Resonance Spectrometry
Spratt, M. P.,Dorn, H. C.
, p. 2038 - 2043 (2007/10/02)
The base-catalyzed reactions of p-fluorobenzoyl chloride provide a convenient method for (19)F NMR analysis of alcohols, phenols, carboxylic acids, amines, and thiols.The (19)F chemical shift and yield data for p-fluorobenzoyl derivatives for nearly 100 compounds are presented.The yield data for these p-fluorobenzoyl derivatives suggest a simple, and in many cases, quantitative method for introducing a fluorine tagging group.The (19)F chemical shifts indicate a wide chemical shift range (ca. 10 ppm) for a large number of compounds.Furthermore, most chemical classes (e.g., phenols, alcohols, etc.) have fairly well resolved chemical shift regions.
