Palladium-catalyzed cross-coupling of electron-poor terminal alkynes with arylboronic acids under ligand-free and aerobic conditions.
Palladium-catalyzed cross-coupling reaction of terminal alkynes with arylboronic acids has been described. In the presence of Pd(OAc)(2) and Ag(2)O, a variety of terminal alkynes, including electron-poor terminal alkynes, smoothly underwent the reaction with numerous boronic acids to afford the corresponding internal alkynes in moderate to good yields. Moreover, this methodology was applied to the synthesis of 1H-isochromenes and diynes. It is noteworthy that the reaction proceeds under ligand-free and relative lower loading Pd conditions, and the maximal TONs (turnover numbers) of the reaction are up to 720,000.
Zhou
Ming-Bo
MB
Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research (Ministry of Education), Hunan Normal University, Changsha 410081, China.
Wei
Wen-Ting
WT
Xie
Ye-Xiang
YX
Lei
Yong
Y
Li
Jin-Heng
JH
D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D004583:Electrons; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
D000480:Alkynes; D001897:Boronic Acids; D009942:Organometallic Compounds; D010165:Palladium