1220015-96-2

Upstream product

• 61589-18-2 N,N-dimethylindoline-1-carboxamide 
• 98-80-6 phenylboronic acid 
• 71-43-2 benzene 
• 496-15-1 1-indoline 
• 2996-92-1 phenyl trimethylsiloxane 
• 595-90-4 tetraphenyltin(IV) 

Relevant academic research and scientific papers

Room-temperature stille coupling of tetraarylstannanes via palladium-catalyzed C-H activation

An effective room-temperature Stille cross-coupling of aryl ureas with tetraarylstannanes via palladium-catalyzed C-H bond activation is reported, providing a mild method for direct arylation of aromatic C-H bonds. Georg Thieme Verlag Stuttgart · New York.

Cationic Pd(II)-catalyzed C-H activation/cross-coupling reactions at room temperature: Synthetic and mechanistic studies

Cationic palladium(II) complexes have been found to be highly reactive towards aromatic C-H activation of arylureas at room temperature. A commercially available catalyst [Pd(MeCN)4](BF4)2 or a nitrile-free cationic palladium(II) complex generated in situ from the reaction of Pd(OAc)2 and HBF4, effectively catalyzes C-H activation/cross-coupling reactions between aryl iodides, arylboronic acids and acrylates under milder conditions than those previously reported. The nature of the directing group was found to be critical for achieving room temperature conditions, with the urea moiety the most effective in promoting facile coupling reactions at an ortho C-H position. This methodology has been utilized in a streamlined and efficient synthesis of boscalid, an agent produced on the kiloton scale annually and used to control a range of plant pathogens in broadacre and horticultural crops. Mechanistic investigations led to a proposed catalytic cycle involving three steps: (1) C-H activation to generate a cationic palladacycle; (2) reaction of the cationic palladacycle with an aryl iodide, arylboronic acid or acrylate, and (3) regeneration of the active cationic palladium catalyst. The reaction between a cationic palladium(II) complex and arylurea allowed the formation and isolation of the corresponding palladacycle intermediate, characterized by X-ray analysis. Roles of various additives in the stepwise process have also been studied.

Direct and site-selective Pd(ii)-catalyzed C-7 arylation of indolines with arylsilanes

The palladium-catalyzed oxidative arylation of indolines with arylsilanes at the C-7 position via C-H bond activation has been reported. This transformation has been applied to a wide range of substrates. It represents a facile access to C-7 arylated indolines, which can be conveniently transformed into C-7 arylated indoles.

Exceptionally mild palladium(II)-catalyzed dehydrogenative C-H/C-H arylation of indolines at the C-7 position under air

An improved method for the dehydrogenative C-H/C-H cross-coupling at the C-7 position of indolines containing a urea as a directing group is reported. The new protocol is a rare example of an aerobic palladium(II)-catalyzed cross dehydrogenative coupling (CDC) reaction that proceeds at low temperature. The use of either Cu(OAc)2 in an open flask or dioxygen (balloon) at 50 °C tolerates indolines not substituted at C-2 and C-3, thereby extending the scope of the previous method that suffers from indoline-to-indole oxidation.

Cationic palladium(II) catalysis: C-H activation/suzuki-miyaura couplings at room temperature

Cationic palladium(II) catalyst realized facile C?H activation of aryl urea with arylboronic acids at room temperature. This reaction is extremely mild to carry out aromatic CH activations through electrophilic substitution.