119999-21-2Relevant articles and documents
Palladium-Catalyzed Three-Component Coupling of Ynamides
Wakamatsu, Hideaki,Takahashi, Ayano,Ishii, Ayaka,Kikuchi, Youhei,Sasaki, Madoka,Saito, Yukako,Natori, Yoshihiro,Yoshimura, Yuichi
supporting information, p. 5299 - 5303 (2020/07/08)
A palladium-catalyzed regioselective three-component coupling of ynamides was developed. The reaction proceeded smoothly to furnish the desired products when carried out at 70 °C in acetonitrile/water with potassium carbonate in the presence of 2.5 mol percent Pd2(dba)3·CHCl3 without a ligand. Various iodides and boronic acids were used in this reaction, and a carbon-carbon bond was formed with satisfactory regioselectivity from the ynamides.
Rhodium-catalyzed cross-coupling of aryl carbamates with arylboron reagents
Nakamura, Keisuke,Yasui, Kosuke,Tobisu, Mamoru,Chatani, Naoto
, p. 4484 - 4489 (2015/03/30)
A new method has been developed for the rhodium-catalyzed cross-coupling of aryl carbamates with organoboron reagents. The use of an NHC ligand bearing a 2-adamantyl group, i.e., I(2-Ad), is essential to the success of the reaction. The reaction involves the rhodium-mediated activation of the relatively inert C(aryl)-O bond of aryl carbamates.
Single-electron-transfer-induced coupling of arylzinc reagents with aryl and alkenyl halides
Shirakawa, Eiji,Tamakuni, Fumiko,Kusano, Eugene,Uchiyama, Nanase,Konagaya, Wataru,Watabe, Ryo,Hayashi, Tamio
, p. 521 - 525 (2014/01/23)
Arylzinc reagents, prepared from aryl halides/zinc powder or aryl Grignard reagents/zinc chloride, were found to undergo coupling with aryl and alkenyl halides without the aid of transition-metal catalysis to give biaryls and styrene derivatives, respectively. In this context, we have already reported the corresponding reaction using aryl Grignard reagents instead of arylzinc reagents. Compared with the Grignard cross-coupling, the present reaction features high functional-group tolerance, whereby electrophilic groups such as alkoxycarbonyl and cyano groups are compatible as substituents on both the arylzinc reagents and the aryl halides. Aryl halides receive a single electron and thereby become activated as the corresponding anion radicals, which react with arylzinc reagents, thus leading to the cross-coupling products. Arylzinc reagents were found to undergo coupling with aryl and alkenyl halides to give biaryl and styrene derivatives, respectively. The cross-coupling, which features high functional-group tolerance, proceeds through a single-electron-transfer mechanism and thus does not require the aid of transition-metal catalysis.
