Electrochemically Driven Tandem Cyclization Reaction of Unsaturated Sulfoximines with Diselenides
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Abstract An electrochemically enabled tandem cyclization reaction of unsaturated sulfoximines with diselenides has been well developed, affording metal‐ and external oxidant‐free access to sulfoximidoyl‐based heterocycles containing selenium in moderate to good yields. With n Bu 4 NBr as the role of catalyst and electrolyte, this methodology shows broad substrate scope and functional group tolerance under mild conditions.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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Abstract A simple and efficient visible‐light‐induced tandem cyclization of 1,6‐enynes with disulfides for the synthesis of functionalized benzofurans was developed. The reaction proceeded smoothly under metal‐free conditions at room temperature in air, providing the desired products in good yields with wide functional group tolerance.
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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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A novel and efficient route for the preparation of 4-carboxylated isoquinolines via a Ag(I) and Cu(I) cocatalyzed tandem reaction of 2-alkynylbenzaldoximes with aldehydes or alcohols in moderate to good yields is described. The reaction proceeds smoothly to produce C-N and C-O bonds in a one-pot procedure with structural complexity and molecular diversity.
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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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