14908-44-2Relevant 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.
supporting information, 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.
Direct Catalytic Symmetrical, Unsymmetrical N,N-Dialkylation and Cyclization of Acylhydrazides Using Alcohols
Thiyagarajan, Subramanian,Gunanathan, Chidambaram
supporting information, p. 6617 - 6622 (2020/09/02)
Herein, direct N,N-dialkylation of acylhydrazides using alcohols is reported. This catalytic protocol provides one-pot synthesis of both symmetrical and unsymmetrical N,N-disubstituted acylhydrazides using an assortment of primary and secondary alcohols w
Products of the Reactions of 1-Aroyl-2,2-dimethylhydrazines with Propargyl and Allyl Bromides
Nakhmanovich,Nizovtseva,Karnaukhova,Komarova,Albanov,Lopyrev
, p. 583 - 585 (2007/10/03)
1-Aroyl-2,2-dimethylhydrazines react with propargyl and allyl bromides to form, respectively, 1,1-dimethy1-1-(2-propyn-1-y1)- and 1,1-dimethy1-1-(2- propen-1-y1)-2-aroylhydrazinium bromides. Treatment of these compounds with an NaOH solution yielded, resp
Reactions of 1,3-dibromopropyne with 1-aroyl-2,2-dimethylhydrazines as a new method for the synthesis of substituted 1,3,4-oxadiazinium bromides
Karnaukhova,Nizovtseva,Nakhmanovich,Albanov,Komarova
, p. 2475 - 2476 (2007/10/03)
Reactions of 1-aroyl-2,2-dimethylhydrazines with 1,3-dibromopropyne in MeOH or MeCN at 20-50 °C yield 2-aryl-6-bromomethylidene-4,4-dimethyl-5H-1,3,4-oxadiazinium bromides.
