60512-56-3Relevant articles and documents
Synthesis of 3,4-bis(Butylselanyl)selenophenes and 4-alkoxyselenophenes promoted by oxone
Hellwig, Paola S.,Guedes, Jonatan S.,Barcellos, Angelita M.,Perin, Gelson,Lenard?o, Eder J.
supporting information, (2021/05/28)
We describe herein an alternative transition-metal-free procedure to access 3,4-bis(butylsela nyl)selenophenes and the so far unprecedented 3-(butylselanyl)-4-alkoxyselenophenes. The protocol involves the 5-endo-dig electrophilic cyclization of 1,3-diynes promoted by electrophilic organosele-nium species, generated in situ through the oxidative cleavage of the Se-Se bond of dibutyl diselenide using Oxone as a green oxidant. The selective formation of the title products was achieved by controlling the solvent identity and the amount of dibutyl diselenide. By using 4.0 equiv of dibutyl diselenide and acetonitrile as solvent at 80?C, four examples of 3,4-bis(butylselanyl)selenophenes were obtained in moderate to good yields (40–78%). When 3.0 equiv of dibutyl diselenide were used, in the presence of aliphatic alcohols as solvent/nucleophiles under reflux, 10 3-(butylselanyl)-4-alkoxyselenophenes were selectively obtained in low to good yields (15–80%).
Pd-Catalyzed Indole Synthesis via C-H Activation and Bisamination Sequence with Diaziridinone
Wang, Jianjun,Sun, Xiaofeng,Hu, Daguo,Shi, Yian
supporting information, p. 7561 - 7565 (2021/10/02)
This work describes an efficient Pd-catalyzed indole synthesis. A wide variety of indoles can be obtained in good yields from readily available vinyl bromides. The reaction likely proceeds through a sequential aryl C-H activation and bisamination of a resulting pallada(II)cycle with diaziridinone.
Expedient Synthesis of Bridged Bicyclic Nitrogen Scaffolds via Orthogonal Tandem Catalysis
Bheemireddy, Narendraprasad Reddy,Biswas, Sovan,Evano, Gwilherm,Maes, Bert U. W.,Van Steijvoort, Ben F.,Waeterschoot, Marjo
supporting information, p. 21988 - 21996 (2021/08/13)
Bridged nitrogen bicyclic skeletons have been accessed via unprecedented site- and diastereoselective orthogonal tandem catalysis from readily accessible reactants in a step economic manner. Directed Pd-catalyzed γ-C(sp3)-H olefination of aminocyclohexane with gem-dibromoalkenes, followed by a consecutive intramolecular Cu-catalyzed amidation of the 1-bromo-1-alkenylated product delivers the interesting normorphan skeleton. The tandem protocol can be applied on substituted aminocyclohexanes and aminoheterocycles, easily providing access to the corresponding substituted, aza- and oxa-analogues. The Cu catalyst of the Ullmann-Goldberg reaction additionally avoids off-cycle Pd catalyst scavenging by alkenylated reaction product. The picolinamide directing group stabilizes the enamine of the 7-alkylidenenormorphan, allowing further product post functionalizations. Without Cu catalyst, regio- and diastereoselective Pd-catalyzed γ-C(sp3)-H olefination is achieved.
