Controlling selectivity in N-heterocycle directed borylation of indoles

Ir-catalyzed functionalization of 2-substituted indoles at the 7-position: nitrogen-directed aromatic borylation.

Ir-catalyzed borylation of 2-substituted indoles selectively yields 7-borylated products in good yields. N-Protection, required for previous functionalizations of 2-substituted indoles, is unnecessary.

Functional group directed C-H borylation.

The direct borylation of hydrocarbons via C-H activation has reached an impressive level of sophistication and efficiency, emerging as a fundamental tool in synthesis because of the versatility offered by organoboron compounds. As a remarkable particularity, the catalytic systems originally developed for these reactions are relatively insensitive to directing effects, and the regioselectivity o...

Directed Selectivity in Organic Synthesis

Nickel-catalyzed borylation of arenes and indoles via C-H bond cleavage.

The first nickel-catalyzed method for the borylation of carbon-hydrogen bonds in arenes and indoles is described. The use of an N-heterocyclic carbene ligand is essential for an efficient reaction, with an N-cyclohexyl-substituted derivative being optimal. This method is readily applied to the gram scale synthesis of 2-borylindole.

A combinatorial scaffold approach toward kinase-directed heterocycle libraries.

A novel strategy for efficient synthesis of various substituted heterocycles as kinase-directed combinatorial libraries is described. The general scheme involves capture of various dichloroheterocycles onto solid support and further elaborations by aromatic substitution with amines at elevated temperature or by anilines, boronic acids, and phenols via palladium-catalyzed cross-coupling reaction...