1361583-02-9Relevant academic research and scientific papers
HBr–DMPU: The First Aprotic Organic Solution of Hydrogen Bromide
Li, Zhou,Ebule, Rene,Kostyo, Jessica,Hammond, Gerald B.,Xu, Bo
supporting information, p. 12739 - 12743 (2017/09/25)
HBr and DMPU (1,3-dimethyl-3,4,5,6-tetrahydro-2-pyrimidinone) form a room-temperature-stable complex that provides a mild, effective, and selective hydrobrominating reagent toward alkynes, alkenes, and allenes. HBr–DMPU could also replace other halogenating reagents in the halo-Prins reaction, ether cleavage, and deoxy-bromination reactions.
Ynamide Carbopalladation: A Flexible Route to Mono-, Bi- and Tricyclic Azacycles
Campbell, Craig D.,Greenaway, Rebecca L.,Holton, Oliver T.,Walker, P. Ross,Chapman, Helen A.,Russell, C. Adam,Carr, Greg,Thomson, Amber L.,Anderson, Edward A.
supporting information, p. 12627 - 12639 (2015/09/01)
Bromoenynamides represent precursors to a diversity of azacycles by a cascade sequence of carbopalladation followed by cross-coupling/electrocyclization, or reduction processes. Full details of our investigations into intramolecular ynamide carbopalladation are disclosed, which include the first examples of carbopalladation/cross-coupling reactions using potassium organotrifluoroborate salts; and an understanding of factors influencing the success of these processes, including ring size, and the nature of the coupling partner. Additional mechanistic observations are reported, such as the isolation of triene intermediates for electrocyclization. A variety of hetero-Diels-Alder reactions using the product heterocycles are also described, which provide insight into Diels-Alder regioselectivity.
Palladium-catalyzed cyclization of bromoenynamides to tricyclic azacycles: Synthesis of trikentrin-like frameworks
Campbell, Craig D.,Greenaway, Rebecca L.,Holton, Oliver T.,Chapman, Helen A.,Anderson, Edward A.
, p. 5187 - 5189 (2014/05/06)
Palladium-catalyzed cascade cyclization of bromoenynamides equipped with an additional alkyne or ynamide substituent affords azatricyclic products. Using 5- to 7-membered ring tethers, this chemistry offers a regiospecific route to highly-functionalized azacycles. Elaboration to the trikentrin B skeleton is achieved from the arylsilane cyclization products. the Partner Organisations 2014.
Reductive cyclization of bromoenynamides with alcohols as hydride source: Synthesis and reactions of 2-amidodienes
Greenaway, Rebecca L.,Campbell, Craig D.,Chapman, Helen A.,Anderson, Edward A.
supporting information, p. 3187 - 3194 (2013/01/15)
Under basic conditions in alcoholic solvents, bromoenynamides undergo palladium-catalyzed cyclization to cyclic 2-amidodienes in good to excellent yields. This process represents the first use of an alcohol as a hydride source in an alkyne carbopalladation/termination sequence, with the site selectivity of the reduction showing a strong dependence on the tethering ring size (5-8), and the nature of the alcohol and base. Reaction of the dienes with a range of dienophiles (including alkenes, alkynes and arynes) under various conditions gives bi- and tricyclic azacycles, which can be further oxidized to the aromatic azacycles. Copyright
Palladium-catalyzed cascade cyclization of ynamides to azabicycles
Greenaway, Rebecca L.,Campbell, Craig D.,Holton, Oliver T.,Russell, C. Adam,Anderson, Edward A.
supporting information; scheme or table, p. 14366 - 14370 (2012/02/04)
Cascade reactions: A modular assembly of azabicycles by using a cascade cyclization/Suzuki coupling/6π-electrocyclization of bromoenynamides is reported (see scheme). The reaction offers a wide substituent scope on the bicyclic aminodiene products, which can be selectively oxidized as a general approach to aromatic azabicycles.
