Ruthenium‐Catalyzed Cascade CH Functionalization of Phenylacetophenones

Abstract

Scheme 1. Cascade CÀH functionalization. DG = directing group, EWG = electron-withdrawing group.[*] Dr.

Ruthenium(II)‐Catalyzed CH Activation with Isocyanates: A Versatile Route to Phthalimides

“…In recent years, ruthenium complexes have emerged as a versatile, less-expensive alternative to commonly used transition metals in CÀH activation chemistry. [10] Along this line, ruthenium(II)-catalyzed cyclometalation followed by migratory insertion of CÀC multiple bonds is well-documented in the literature. [10] However, in striking contrast to rhodium or rhenium catalysis, [11] the addition to polar CÀHet multiple bonds is extremely rare in ruthenium-catalyzed transformations and was hitherto only accomplished with strongly coordinating arylpyridines, which are unfortunately extremely difficult to remove or modify.…”

“…[10] Along this line, ruthenium(II)-catalyzed cyclometalation followed by migratory insertion of CÀC multiple bonds is well-documented in the literature. [10] However, in striking contrast to rhodium or rhenium catalysis, [11] the addition to polar CÀHet multiple bonds is extremely rare in ruthenium-catalyzed transformations and was hitherto only accomplished with strongly coordinating arylpyridines, which are unfortunately extremely difficult to remove or modify. [12] In consideration of the practical importance of CÀH activations with synthetically useful auxiliaries, [8a] we explored readily available amides for CÀH functionalization with isocyanates (Scheme 1).…”

Automatic Fiber Thickness Measurement in Scanning Electron Microscopy Images Validated Using Synthetic Data

“…Reactions based on this transformation type usually require appropriate directing groups, transition metals as the catalysts and stoichiometric amounts of external oxidants in order to achieve CH regioselectivity and good reactivity 1,2. A broad range of directing groups, including amides,3 carboxy,4 hydroxy,5 triflamide,6 amidine7 and acetophenone moieties,8 have been tested in these reactions. The N H imidate was reported by Glorius in 2013 as a novel directing group in CH activation,9 but it has not yet to be tested in the oxidative alkenylation/annulation cascade reaction.…”

Oxidative Alkenylation/Annulation of Benzimidates via Ruthenium(II)‐Catalyzed CH Activation to Generate 3‐Methyleneisoindolin‐1‐ones

“…[1,2] Reactions based on this transformation type usually require appropriate directing groups, transition metals as the catalysts and stoichiometric amounts of external oxidants in order to achieve C À H regioselectivity and good reactivity. [1,2] A broad range of directing groups, including amides, [3] carboxy, [4] hydroxy, [5] triflamide, [6] amidine [7] and acetophenone moieties, [8] have been tested in these reactions. The N À H imidate was reported by Glorius in 2013 as a novel directing group in C À H activation, [9] but it has not yet to be tested in the oxidative alkenylation/annulation cascade reaction.…”