Rhodium/N‐Heterocyclic Carbene Catalyzed Direct Intermolecular Arylation of sp² and sp³ CH Bonds with Chelation Assistance

Abstract

Von Pyridylgruppen gelenkt gelingt die im Titel genannte Reaktion (siehe Schema; IMes=1,3‐Bis(2,4,6‐trimethylphenyl)imidazol‐2‐yliden). Die Reaktion an C sp 3‐ oder C sp 2‐H‐Bindungen von Aryl‐, Vinyl‐ oder Alkylsubstraten mit 2‐Pyridylgruppen liefert die mono‐ oder diarylierten Produkte unter milden Bedingungen in ausgezeichneten Ausbeuten.

Water‐Soluble IrIII N‐Heterocyclic Carbene Based Catalysts for the Reduction of CO2 to Formate by Transfer Hydrogenation and the Deuteration of Aryl Amines in Water

“…Also, it was recently described that a dirhodium(II) complex was able to selectively deuterate benzo[h]quinoline at the C10-position, although in this case the reaction needed a stoichiometric amount of the dimetallic species (the reaction is not catalytic) and base. [18] Aiming to study the same process with our new water-soluble catalysts 2 and 3, and having proved its activity in C À H activation processes such as those shown in Table 2 for the reduction of CO 2 with iPrOH, we thought that these two catalysts should have a high chance of activity in this reaction. The results that we obtained are listed in Table 3.…”

Cross‐Coupling of Heteroarenes by CH Functionalization: Recent Progress towards Direct Arylation and Heteroarylation Reactions Involving Heteroarenes Containing One Heteroatom

“…[199] Chang and co-workers had previously employed an RhA C H T U N G T R E N N U N G (OAc) 2 asc.wiley-vch.de mides. [201] As shown in Scheme 156, both aryl bromides bearing electron-withdrawing and electron-donating substituents could be employed for these couplings, although use of the latter slightly slowed the reaction rate.…”

“…[201] In 2010, Luo and Yu developed an efficient and economically attractive catalyst system, more simple than that developed by Chang and co-workers, [201] for the C-10 arylation of benzo[h]quinoline (305). [202] They used the RuCl 3 ·H 2 O/PPh 3 /Na 2 CO 3 /NMP catalytic system and employed aryl chlorides as reaction partners.…”

Cp*RhIII‐katalysierte Arylierung von C(sp3)‐H‐Bindungen

“…Tr iarylmethane und ihre Derivate finden breite Anwendung in den Materialwissenschaften und der medizinischen Chemie, [14] allgemeine Synthesen [15,16] unsymmetrischer Tr iarylmethane durch Arylierung sekundärer C-H-Bindungen sind jedoch nicht verbreitet. [17] [18] Wirh aben eine Rh III -katalysierte Arylierung von C(sp 3 )-H-Bindungen entwickelt, einschließlich der Aktivierung schwieriger nichtaktivierter homobenzylischer C(sp 3 )-H-Bindungen und sekundärer benzylischer C(sp 3 )-H-Bindungen. Verschiedene 2-Alkylpyridin-Derivate kçnnen mit diversen Tr iarylboroxinen umgesetzt werden, um neue C(sp 3 )-Aryl-Bindungen zu knüpfen und funktionalisierte Pyridinderivate zu erhalten.…”