5194-49-0Relevant academic research and scientific papers
Iron-catalyzed stereoselective haloamidation of amide-tethered alkynes
Liu, Jin-Biao,Ren, Miaofeng,Lai, Xiaojing,Qiu, Guanyinsheng
supporting information, p. 4259 - 4262 (2021/05/05)
In this work, by usingN-methoxybenzamides as efficient acyl nitrene precursors, an iron-catalyzed formalcis-haloamidation of alkyne is reported. Without assistance of additives, the reaction worked well in the presence of 50 mol% FeCl3or FeBr3, leading to a series of chloro/bromo-containing isoindolin-5-ones with high efficiency and wide reaction scope. In the reaction, the iron-facilitated haloamidation proceeds through a halo anion-participating concerted [3+2] cyclization to release the final products. The key intermediate ferric acyl nitreneAis generatedin situfrom a formal removal of MeOH.
Phosphazene Superbase-Mediated Regio- and Stereoselective Iodoaminocyclization of 2-(1-Alkynyl)benzamides for the Synthesis of Isoindolin-1-ones
Mehta, Saurabh,Brahmchari, Dhirendra
, p. 5492 - 5503 (2019/05/10)
Phosphazene superbase P4-t-Bu mediated iodoaminocyclization of 2-(1-alkynyl)benzamides is reported. The reaction works under ambient conditions and instantaneously results in the synthesis of isoindolin-1-ones in 65-97% yields, in a regio- and stereoselective manner. The exclusive formation of products with Z-geometry (across the exo C?C bond) has been confirmed through X-ray crystallography. The methodology also provides an easy access to aristolactams, an important class of natural products. This has been successfully demonstrated by synthesizing two aristolactam derivatives (including Cepharanone B).
Ir(III)-Catalyzed Stereoselective Haloamidation of Alkynes Enabled by Ligand Participation
Hong, Seung Youn,Son, Junsoo,Kim, Dongwook,Chang, Sukbok
, p. 12359 - 12363 (2018/10/02)
Described herein is the application of a strategy of ligand participation for the Ir-catalyzed imido transfer into alkynes. On the basis of a stoichiometric [3 + 2] cycloaddition of Cp?Ir(III)(κ2-N,O-chelate) with alkynyl dioxazolone, a catalyt
