195624-82-9Relevant academic research and scientific papers
Spatial anion control on palladium for mild C-H arylation of arenes
Dhankhar, Jyoti,González-Fernández, Elisa,Dong, Chao-Chen,Mukhopadhyay, Tufan K.,Linden, Anthony,?ori?, Ilija
supporting information, p. 19040 - 19046 (2020/11/13)
C-H arylation of arenes without the use of directing groups is a challenge, even for simple molecules, such as benzene. We describe spatial anion control as a concept for the design of catalytic sites for C-H bond activation, thereby enabling nondirected C-H arylation of arenes at ambient temperature. The mild conditions enable late-stage structural diversification of biologically relevant small molecules, and site-selectivity complementary to that obtained with other methods of arene functionalization can be achieved. These results reveal the potential of spatial anion control in transition-metal catalysis for the functionalization of C-H bonds under mild conditions.
Synthesis of Tetrahydroisoquinolines through an Iron-Catalyzed Cascade: Tandem Alcohol Substitution and Hydroamination
Marcyk, Paul T.,Cook, Silas P.
supporting information, p. 6741 - 6744 (2019/09/07)
Rapid assembly of saturated nitrogen heterocycles - the synthetically more challenging variants of their aromatic relatives - can expedite the synthesis of biologically relevant molecules. Starting from a benzylic alcohol tethered to an unactivated alkene, an iron-catalyzed tandem alcohol substitution and hydroamination provides access to tetrahydroisoquinolines in a single synthetic step. Using a mild iron-based catalyst, the combination of these operations forms two carbon-nitrogen bonds and provides a unique annulation strategy to access this valuable core.
Design of New Ligands for the Palladium-Catalyzed Arylation of α-Branched Secondary Amines
Park, Nathaniel H.,Vinogradova, Ekaterina V.,Surry, David S.,Buchwald, Stephen L.
supporting information, p. 8259 - 8262 (2015/07/07)
In Pd-catalyzed C-N cross-coupling reactions, α-branched secondary amines are difficult coupling partners and the desired products are often produced in low yields. In order to provide a robust method for accessing N-aryl α-branched tertiary amines, new catalysts have been designed to suppress undesired side reactions often encountered when these amine nucleophiles are used. These advances enabled the arylation of a wide array of sterically encumbered amines, highlighting the importance of rational ligand design in facilitating challenging Pd-catalyzed cross-coupling reactions.
A stereoselective intramolecular Diels-Alder strategy for the tricyclo[9.3.1.03,8]pentadecane core of aromatic C-ring taxanes
Smil, David V.,Laurent, Alain,Spassova, Nidejda S.,Fallis, Alex G.
, p. 5129 - 5132 (2007/10/03)
A stereoselective Lewis acid-catalyzed and chelation controlled intramolecular Diels-Alder entry into the tricyclo[9.3.1.03,8]pentadecane core of aromatic C-ring taxanes is described. The approach affords an efficient, high yield, access to aromatic C-ring taxanes variably functionalized at the C2, C4, C5, and C9 positions.
