103449-03-2Relevant academic research and scientific papers
N-Ammonium Ylide Mediators for Electrochemical C-H Oxidation
Saito, Masato,Kawamata, Yu,Meanwell, Michael,Navratil, Rafael,Chiodi, Debora,Carlson, Ethan,Hu, Pengfei,Chen, Longrui,Udyavara, Sagar,Kingston, Cian,Tanwar, Mayank,Tyagi, Sameer,McKillican, Bruce P.,Gichinga, Moses G.,Schmidt, Michael A.,Eastgate, Martin D.,Lamberto, Massimiliano,He, Chi,Tang, Tianhua,Malapit, Christian A.,Sigman, Matthew S.,Minteer, Shelley D.,Neurock, Matthew,Baran, Phil S.
, p. 7859 - 7867 (2021/05/26)
The site-specific oxidation of strong C(sp3)-H bonds is of uncontested utility in organic synthesis. From simplifying access to metabolites and late-stage diversification of lead compounds to truncating retrosynthetic plans, there is a growing need for new reagents and methods for achieving such a transformation in both academic and industrial circles. One main drawback of current chemical reagents is the lack of diversity with regard to structure and reactivity that prevents a combinatorial approach for rapid screening to be employed. In that regard, directed evolution still holds the greatest promise for achieving complex C-H oxidations in a variety of complex settings. Herein we present a rationally designed platform that provides a step toward this challenge using N-ammonium ylides as electrochemically driven oxidants for site-specific, chemoselective C(sp3)-H oxidation. By taking a first-principles approach guided by computation, these new mediators were identified and rapidly expanded into a library using ubiquitous building blocks and trivial synthesis techniques. The ylide-based approach to C-H oxidation exhibits tunable selectivity that is often exclusive to this class of oxidants and can be applied to real-world problems in the agricultural and pharmaceutical sectors.
Extraction and complexation of copper(II) with para-tert-butylbenzhydrazide and its N',N'-dimethyl derivative
Gusev,Muksinova,Radushev
experimental part, p. 679 - 684 (2012/10/07)
The extraction of copper(II) with the para-tert-butylbenzoic acid hydrazide and related N',N'dimethyl derivative was studied. The composition and structure of the extracted complexes were determined, the mechanism of extraction of copper(II) in different
New reactions of hydrazides. Part 1: Directed ortho- and lateral metalation of aromatic carbocyclic and heterocyclic systems
McCombie, Stuart W.,Lin, Sue-Ing,Vice, Susan F.
, p. 8767 - 8770 (2007/10/03)
Aromatic and heterocyclic 2,2-dialkylhydrazides undergo directed metalation with 2 equivalents of n-, s- or t-BuLi, and the resulting C,N- dilithio species react with a variety of electrophiles. The products may be readily converted to the corresponding carboxylic acids or esters by oxidation with manganese dioxide in water or methanol containing acetic acid.
