1613027-85-2

Upstream product

• 7127-19-7 2-phenyl-1,3-oxazoline 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 1570134-48-3 N-(2-(4,5-dihydrooxazol-2-yl)phenyl)benzamide 
• 24424-99-5 di-tert-butyl dicarbonate 
• 36016-38-3 tert-Butyl N-hydroxycarbamate 
• 1613027-54-5 methyl 4-[{(tert-butoxycarbonyl)amino}oxycarbonyl]benzoate 
• 870-46-2 t-butoxycarbonylhydrazine 
• 3416-93-1 2-(4,5-Dihydro-1,3-oxazol-2-yl)aniline 
• 1885-29-6 anthranilic acid nitrile 

Relevant academic research and scientific papers

A Facile Access to Primary Alkylamines and Anilines via Ir(III)-Catalyzed C-H Amidation Using Azidoformates

Described herein is the development of Ir(III)-catalyzed direct C-H amidation using azidoformates as a readily deprotectable amino source. Substrates with unactivated methyl C(sp3)-H and aromatic or olefinic C(sp2)-H bonds were smoothly reacted by the iridium-based catalyst system to provide the corresponding primary alkylamines and anilines upon the subsequent removal of N-protecting groups, such as Boc, Fmoc, Cbz, pNZ, or Troc. A brief mechanistic study and synthetic applications are also presented.

Rhodium-Catalyzed N-tert-Butoxycarbonyl (Boc) Amination by Directed C H Bond Activation

N-tert-Butoxycarbonyl azide (BocN3) was shown to be an efficient and economic source for the directed introduction of N-Boc protected amino groups into the thiophene and benzene nucleus. Yields for the amination of 2-pyridin-2-ylthiophenes (10 examples) were 52–88%. For the amination of the respective benzenes (10 examples) yields between 54% and 99% were recorded with an improved reactivity observed for substrates that bear an electron-withdrawing group. The reaction was applied to short total syntheses of the indoloquinoline alkaloids quindoline and cryptolepine. The facile removal of the Boc protecting group was the key to the success of the syntheses. The scope of the reaction was extended to a C(sp3) H bond amination and to the amination of 2-phenyloxazoline. For the amination of 2-pyridin-2-ylbenzene a kinetic deuterium isotope effect of 2.0 was determined. (Figure presented.) .

Cu(II)-mediated ortho C-H alkynylation of (hetero)arenes with terminal alkynes

Cu(II)-promoted ortho alkynylation of arenes and heteroarenes with terminal alkynes has been developed to prepare aryl alkynes. A variety of arenes and terminal alkynes bearing different substituents are compatible with this reaction, thus providing an alternative disconnection to Sonogashira coupling.

N -substituted hydroxylamines as synthetically versatile amino sources in the iridium-catalyzed mild C-H amidation reaction

N-Substituted hydroxylamines such as aroyloxy- or acyloxycarbamates were successfully employed as synthetically versatile amino precursors in the iridium-catalyzed direct C-H amidation of arenes. The reaction proceeds smoothly at room temperature over a broad range of substrates with high functional group tolerance to afford N-substituted arylamine products.