Ruthenium Complex Catalyzed Direct Ortho Arylation and Alkenylation of Aromatic Imines with Organic Halides

Abstract

[reaction: see text] The ortho position of the aromatic ring of imino group substituted aromatic compounds is directly arylated and alkenylated with organic halides in the presence of a catalytic amount of a ruthenium(II)-phosphine complex.

Ruthenium N‐heterocyclic–carbene catalyzed diarylation of arene CH bond

“…In particular, a general protocol for ruthenium-catalyzed arylations [18,20] employing inexpensive, but less reactive, aryl chlorides has proven elusive. [21] Based on these findings and our continuing interest in developing more efficient and stable catalysts, we wished to examine whether we could influence the catalytic activity of ruthenium-1,3-dialkylimidazolin-2-ylidene complexes for the arylation of 2-phenylpyridine. (Scheme 1).…”

A Phosphino‐Carboxylic Acid‐Based Ru Dimeric Complex

“…In order to confirm this trend in a second test reaction, complexes [2] and [4] were evaluated as catalysts in the notorious Ru‐catalyzed arylation of phenyl pyridines (Scheme ) . Likewise, no significant differences were observed in terms of catalytic behavior, both ligand systems affording high yields of the C–H arylated products.…”

“…For all structures vibrational spectra are calculated, scaled with the factor 0.9608 and convolved with a Gaussian (FWHM = 15 cm –1 ). Characterization of C1–N bicarbazole product: see ref . UV/Vis/Luminescence spectroscopy: For all measurements, only spectroscopy grade solvents from Fluka were used.…”

Chemoselective one‐pot synthesis of terphenyl derivatives by sequential directed C―H functionalization–Suzuki coupling

“…During the last few years, transition‐metal‐catalyzed ortho ‐arylation of aryl C―H bonds has emerged as a fascinating area rich in challenges and opportunities. With a directing group such as pyridine, imine, acetamine, carboxylic acid, cyano or oxazoline, an ortho ‐C―H bond can be highly regioselectively functionalized under palladium, ruthenium or rhodium catalysis . Aryl iodides, iodine(III) reagents, arylboronic acids and aryltrimethylsilanes were regularly used as arylating agents in C―H arylation reactions.…”