28748-21-2

Upstream product

• 611-32-5 8-methylquinoline 
• 696-62-8 para-iodoanisole 
• 5720-07-0 4-methoxyphenylboronic acid 

Relevant academic research and scientific papers

Ru(II)-Catalyzed Chemoselective C(sp3)-H Monoarylation of 8-Methyl Quinolines with Arylboronic Acids

The transition-metal-promoted C-H activation has become an efficient as well as atom-economic methodology for the synthesis of a wide array of organic molecules, but the cost of the metal catalyst and selectivity remain the major challenges. Herein, the first [Cl2Ru(p-cymene)]2-catalyzed direct monoarylation of unactivated C(sp3)-H bonds of 8-methyl quinolines with arylboronic acids to synthesize diarylmethane compounds is presented. The transformation shows a broad substrate scope with high chemoselectivity for the synthesis of 8-benzyl quinolines. In the preliminary mechanistic studies, control experiments, deuterium labeling experiments, and kinetic studies have been performed.

Cp*RhIII-Catalyzed Sterically Controlled C(sp3)?H Selective Mono- and Diarylation of 8-Methylquinolines with Organoborons

Herein, the RhIII-catalyzed selective monoarylation and diarylation (symmetrical and unsymmetrical) of 8-methylquinolines with organoboron reagents are disclosed. The selective monoarylation of primary C(sp3)?H bonds is achieved by using 7-substituted 8-methylquinolines or by changing the quantity of the aryl boronic acids. The method is also applicable for the arylation of 2-ethylpyridines, and the heteroarylation with thiophene-2-ylboronic acids. Symmetrical and unsymmetrical diarylation of 8-methylquinolines have been carried out in one-pot and sequential manner, respectively. Late-stage monoarylation of oxime derivatives and gram-scale synthesis of monoarylated products has also been carried out. A mechanistic study revealed that the current reaction is first order with respect to both reactants and a five-membered rhodacycle intermediate may be involved in the catalytic cycle.

CpRhIII-Catalyzed Arylation of C(sp3) Bonds

The first CpRhIII-catalyzed arylation of unactivated C(sp3) bonds is presented. The unactivated primary C(sp3) bond of 2-alkylpyridines can be activated by RhIII and further reacts with triarylboroxines to efficiently build new C(sp3)-aryl bonds. The methodology also provides a facile and efficient synthesis of unsymmetrical triarylmethanes by RhIII-catalyzed C(sp3) arylation of diarylmethanes. Unactivated! The unactivated primary C(sp3) bond of 2-alkylpyridines can be activated by RhIII and then react with triarylboroxines to efficiently build new C(sp3)-aryl bonds (see scheme, DG=directing group, FG=functional group). The methodology also provides a facile and efficient synthesis of unsymmetrical triarylmethanes by RhIII-catalyzed C(sp3) arylation.

An organic cation as a silver(i) analogue for the arylation of sp 2 and sp3 C-H bonds with iodoarenes

Reactions promoted by stoichiometric amounts of silver salts suffer from high cost, limited availability and raise environmental concerns. This manuscript describes studies leading to the discovery of a general replacement for silver with an inexpensive and convenient organic salt in palladium catalyzed direct C(sp2)-H and C(sp3)-H arylation reactions.