NIS-Mediated Oxidative Lactonization of 2-Arylbenzoic Acids for the Synthesis of Dibenzopyranones under Metal-Free Conditions
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A series of dibenzopyranones were synthesized from 2-arylbenzoic acids by a radical oxidative cyclization procedure mediated by N-iodosuccinimide (NIS). The methodology is distinguished by its practicality in terms of its wide substrate scope, good functional group tolerance, and mild reaction conditions without the use of transition metals.Keywords:
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The synthesis of alkenylated-o-carboranes via photoalkenylation of iodocarboranes with unactivated alkenes has been achieved. This strategy features a transition metal-free protocol, a light-promoted reaction under mild reaction conditions, broad substrate scope and good functional group tolerance. Control experiments suggest that the reaction may involve the cage C-centered radical species.
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An efficient approach for the synthesis of benzo-fused pyridoindolone derivatives via a one-pot copper catalyzed tandem reaction of 2-iodobenzamides with 2-iodobenzylcyanides has been developed. Using this protocol, benzo-fused pyridoindolone derivatives are obtained in high yields in a relatively short period of time under mild reaction conditions. To the best of our knowledge, this is the first approach where one can synthesize free indole N–H benzo-fused pyridoindolones. Also, both indole and pyridone cores are constructed during the course of the reaction. The methodology shows good functional group tolerance and allows synthesis of thiophene-fused pyridoindolones and fused indolobenzonaphthyridone derivatives.
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Abstract Herein we report a protocol for commercial available oxone‐mediated nitration cyclization between 1,6‐enynes and Cu(NO 3 ) 2 . This strategy shows attractive characteristics such as mild reaction conditions, operational simplicity, broad substrates scope with good to excellent yields and high functional group tolerance. The reaction provides a regioselective way toward the formation of a new C−N and C−C bonds in one step. Mechanistic studies reveal that the procedure undergoes a radical process.
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A direct C–H thiocyanation of imidazo[1,2‐ a ]pyridines, and a practical sequential one‐pot condensation/C–H thiocyanation process, using a combination of N ‐chlorosuccinimide/NaSCN for the synthesis of 3‐thiocyanatoimidazo[1,2‐ a ]pyridines have been developed. The reactions are environmentally friendly, and easy to carry out. They use readily available starting materials and mild reaction conditions, show a wide functional group tolerance, and give good to excellent yields.
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Abstract A novel and straightforward strategy for the construction of versatile densely functionalized aryl α‐keto esters is disclosed through a one‐pot and efficient [4+2] benzannulation reaction of α‐cyano‐β‐methylenones and ynediones, which could be synthesized easily from the corresponding starting materials. This protocol features high yield, mild metal‐free reaction condition, high atom economy, high functional‐group tolerance, easy handing and gram‐scale synthesis.
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An easily available chiral ligand ( S)- 1 is found to activate the nucleophilic reaction of the arylzincs prepared in situ from the reaction of aryl iodides with Et(2)Zn. Both high yields and high enantioselectivity (up to >99% ee) for the reaction of these arylzincs with a variety of aldehydes are obtained. The mild reaction conditions and the good functional group tolerance make this catalytic asymmetric process synthetically useful.
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