Scope and Regioselectivity of Iridium-Catalyzed C–H Borylation of Aromatic Main-Chain Polymers

Autor:	Ying Chang, Se Hye Kim, Hanniel H. Lee, Tae Soo Jo, Chulsung Bae
Rok vydání:	2013
Předmět:	Polymers and Plastics Organic Chemistry Arylene Regioselectivity Ether Borylation Medicinal chemistry Coupling reaction Sulfone Inorganic Chemistry chemistry.chemical_compound chemistry Materials Chemistry Electronic effect Boronic acid
Zdroj:	Macromolecules. 46:1754-1764
ISSN:	1520-5835 0024-9297
Popis:	An efficient functionalization of aromatic main-chain polymers was established using a combination of iridium-catalyzed borylation of aromatic C–H bonds and the Suzuki–Miyaura coupling reaction. Comparative studies of various iridium catalysts and borylation reagents show that [Ir(OMe)(COD)]2 is significantly more active than [IrCl(COD)]2, and bis(pinacolato)diboron induces higher efficiency than pinacolborane. The regioselectivity of the borylation was investigated using model compounds that mimic the repeating unit structure of poly(arylene ether sulfone). The C–H bonds of the sulfone model compound were more reactive than those of the bisphenol model compound, and the borylation occurred preferentially at the meta position to the sulfone moiety owing to steric hindrance and electronic effects. The glass transition temperature of the borylated polymer increases with increasing concentration of pinacolboronic ester group. The pinacolboronic ester group could be conveniently converted to boronic acid [B(O...
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::57f040fa9b7a7d7a834720654594001e https://doi.org/10.1021/ma302588a Zobrazit plný text záznamu