Ir(iii)-catalyzed thioether directed arene C–H alkenylation

Abstract

In this study, we demonstrate an Ir(iii)-catalyzed thioether directed alkenylation of arene C–H bonds under mild reaction conditions.

HFIP in Organic Synthesis

“…Among C–H functionalizations, C­(sp 2 )- and C­(sp 3 )-alkenylation reactions are important synthetic methods, which typically take advantage of DGs, transition metals, and HFIP as the solvent. In most cases, yields drastically increase when HFIP is utilized in comparison to other solvents, and in some cases, its roles are clearly defined. ,− …”

“…NMR studies indicated strong hydrogen bonding interactions between the pyrimidine DG and HFIP. Furthermore, pyrimidine-based DGs were optimized for the meta -C–H allylation, cyanation, alkylation, alkynylation, and deuteration of arenes. , An Ir­(III)-catalyzed thioether-directed ortho- C–H alkenylation provided mono- or dialkenylated aryl thioethers (Scheme b) . HFIP delivered the best yield of product in the optimization stages, outperforming DCE, acetone, diethyl ether, and trifluorotoluene.…”

State of the Art and Perspectives of Hierarchical Zeolites: Practical Overview of Synthesis Methods and Use in Catalysis

“…Mesopore size control was done by alkalinity variation. [ 217 ] Sashkina et al. attempted changes in the H 2 O/SiO 2 ratio of the precursor solution in a hydrothermal synthesis to get ZSM‐5 nanocrystalline aggregates.…”

Iridium(III)-Catalyzed Branch-Selective C–H Alkenylation of Aniline Derivatives with Alkenes

“…The significance of oxidative C–H alkenylation reactions with alkenes to form C–C bonds via dual C–H bond activation, which is referred to as the Fujiwara–Moritani reaction, is in widespread use because of its high atom and step economy . Various transition metals, such Pd, Rh, Ru, and Ir have been extensively used as catalysts in such C–H alkenylation reactions mainly using a directing group strategy (Scheme a) . Despite the remarkable successes in linear-selective C–H alkenylation, the synthesis of branched alkenes via branch-selective C–H alkenylation has remained undeveloped.…”