35309-06-9Relevant academic research and scientific papers
Gold-Catalyzed Proto- and Deuterodeboronation
Barker, Graeme,Webster, Stacey,Johnson, David G.,Curley, Rachel,Andrews, Matthew,Young, Paul C.,MacGregor, Stuart A.,Lee, Ai-Lan
, p. 9807 - 9816 (2015/11/03)
A mild gold-catalyzed protodeboronation reaction, which does not require acid or base additives and can be carried out in "green" solvents, is described. As a result, the reaction is very functional-group-tolerant, even to acid- and base-sensitive functional groups, and should allow for the boronic acid group to be used as an effective traceless directing or blocking group. The reaction has also been extended to deuterodeboronations for regiospecific ipso-deuterations of aryls and heteroaryls from the corresponding organoboronic acid. Based on density functional theory calculations, a mechanism is proposed that involves nucleophilic attack of water at boron followed by rate-limiting B-C bond cleavage and facile protonolysis of a Au-σ-phenyl intermediate.
Direct coupling of arenes and iodoarenes catalyzed by a rhodium complex with a strongly π-accepting phosphite ligand
Yanagisawa, Shuichi,Sudo, Tomoko,Noyori, Ryoji,Itami, Kenichiro
, p. 6073 - 6081 (2008/09/21)
A new rhodium-based catalytic system for the direct C-H coupling of arenes and iodoarenes that shows high activity with reasonably broad scope was developed. Under the catalytic influence of RhCl(CO){P[OCH(CF3)2]3}2 and Ag2CO3, the direct C-H arylation of heteroarenes and arenes took place with iodoarenes to afford a range of biaryls in good to excellent yields with high regioselectivity. Thiophenes, furans, pyrroles, indoles, and alkoxybenzenes are applicable to this arylation protocol.
