227080-13-9Relevant academic research and scientific papers
Effects of monodentate oxazoline ligands in Ni/Al-catalyzed regioselective cyclotrimerization of enones and alkynes
Ikeda, Shin-Ichi,Kondo, Hirokazu,Mori, Naoyoshi
, p. 815 - 816 (2000)
A nickel and aluminium system including monodentate oxazoline ligands catalyzed the regioselective cyclotrimerization of enones and alkynes.
Catalytic β C-H amination: Via an imidate radical relay
Stateman, Leah M.,Wappes, Ethan A.,Nakafuku, Kohki M.,Edwards, Kara M.,Nagib, David A.
, p. 2693 - 2699 (2019/03/06)
The first catalytic strategy to harness imidate radicals for C-H functionalization has been developed. This iodine-catalyzed approach enables β C-H amination of alcohols by an imidate-mediated radical relay. In contrast to our first-generation, (super)stoichiometric protocol, this catalytic method enables faster and more efficient reactivity. Furthermore, lower oxidant concentration affords broader functional group tolerance, including alkenes, alkynes, alcohols, carbonyls, and heteroarenes. Mechanistic experiments interrogating the electronic nature of the key 1,5 H-atom transfer event are included, as well as probes for chemo-, regio-, and stereo-selectivity.
Catalytic Alkene Difunctionalization via Imidate Radicals
Nakafuku, Kohki M.,Fosu, Stacy C.,Nagib, David A.
, p. 11202 - 11205 (2018/09/12)
The first catalytic strategy to harness imidate radicals has been developed. This approach enables alkene difunctionalization of allyl alcohols by photocatalytic reduction of their oxime imidates. The ensuing imidate radicals undergo consecutive intra- and intermolecular reactions to afford (i) hydroamination, (ii) aminoalkylation, or (iii) aminoarylation, via three distinct radical mechanisms. The broad scope and utility of this catalytic method for imidate radical reactivity is presented, along with comparisons to other N-centered radicals and complementary, closed-shell imidate pathways.
Nickel-catalyzed ligand-free synthesis of benzoxazoles and oxazolines via isocyanide insertion
Wang, Jin-Mei,Jiang, Xiao,Tang, Ting,Zhu, Yong-Ming,Shen, Jing-Kang
, p. 1441 - 1453 (2014/07/07)
A novel and efficient route to benzoxazoles and oxazolines involving a nickel-catalyzed three-component coupling reaction of iodobenzene, an amino alcohol and tert-butyl isocyanide has been developed. A wide array of products have been prepared in good to excellent yields in the absence of ligand.
Allenes. Part 44. Formation of Oxazolines and Benzoxazoles from Allenic nitriles and amides and from Phenylpropynenitrile.
Fomum, Z. Tanee,Nkengfack, A. Ephrem,Mpango, George W. P.,Landor, Stephen R.,Landor, Phyllis D.
, p. 901 - 924 (2007/10/02)
Michael addition of ethanolamines and 2-aminophenol to allenic nitriles, allenic amides and phenylpropynenitrile gives enaminic nitriles and amides which at 290 deg - 320 deg yield oxazolines and benzoxazoles.
