Au-Catalyzed Formation of Functionalized Quinolines from 2-Alkynyl Arylazide Derivatives
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A new method for converting 2-alkynyl arylazide derivatives into functionalized polysubstituted quinolines following a gold-catalyzed 1,3-acetoxy shift/cyclization/1,2-group shift sequence has been developed. This transformation proceeds under mild reaction conditions, is efficient, and tolerates a large variety of functional groups.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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A safe, green and functional-group-tolerant flow version of the direct amide bond formation mediated by Grignard reagents (the Bodroux reaction) is described. The procedure can be applied to a wide variety of primary and secondary amines and anilines, as well as to aromatic and aliphatic esters. The flow approach leads to improved yields and selectivities in the reaction, which has a sustainable purification procedure and a simple scale-up. This reaction represents an efficient and green alternative to the use of alkylaluminium and metal-catalyzed procedures.
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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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Mild cross-coupling reaction between benzylboronic esters with carbonyl compounds and some imines was achieved under visible-light-induced iridium-catalyzed photoredox conditions. Functional group tolerance was demonstrated by 51 examples, including 13 heterocyclic compounds. Gram-scale reaction was realized through the use of computer-controlled continuous flow photoreactors.
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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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Herein, a novel, practical, and green synthetic method using readily available 1,3-enynes with sulfonyl hydrazides and I2 through tert-butyl hydroperoxide (TBHP)-mediated 1,4-sulfonyliodination has been developed for synthesizing various tetrasubstituted allenyl iodides under metal-free conditions. Notably, the proposed method exhibits a broad substrate scope, operational simplicity, tolerance to air, high functional-group tolerance, satisfactory yields, and excellent regioselectivity as well as involves the use of cost-effective reagents such as green oxidants.
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