Regioselective C-H Hydroarylation of Internal Alkynes with Arenecarboxylates: Carboxylates as Deciduous Directing Groups.
In the presence of catalytic [Ru(p-cym)I2 ]2 and the base guanidine carbonate, benzoic acids react with internal alkynes to give the corresponding 2-vinylbenzoic acids. This alkyne hydroarylation is generally applicable to diversely substituted electron-rich and electron-poor benzoic and acrylic acids. Aryl(alkyl)acetylenes react regioselectively with formation of the alkyl-branched hydroarylation products, and propargylic alcohols are converted into γ-alkylidene-δ-lactones. The hydroarylation can also be conducted decarboxylatively with a different choice of catalyst and reaction conditions. This reaction variant, which does not proceed via intermediate formation of 2-vinylbenzoic acids, opens up a regioselective, waste-minimized synthetic entry to vinylarenes.
FB Chemie-Organische Chemie, Technische Universität Kaiserslautern, Erwin-Schrodinger-Str. Geb. 54, 67663, Kaiserslautern, Germany.
Liangbin
L
Huang
FB Chemie-Organische Chemie, Technische Universität Kaiserslautern, Erwin-Schrodinger-Str. Geb. 54, 67663, Kaiserslautern, Germany.
Agostino
A
Biafora
FB Chemie-Organische Chemie, Technische Universität Kaiserslautern, Erwin-Schrodinger-Str. Geb. 54, 67663, Kaiserslautern, Germany.
Guodong
G
Zhang
FB Chemie-Organische Chemie, Technische Universität Kaiserslautern, Erwin-Schrodinger-Str. Geb. 54, 67663, Kaiserslautern, Germany.
Valentina
V
Bragoni
FB Chemie-Organische Chemie, Technische Universität Kaiserslautern, Erwin-Schrodinger-Str. Geb. 54, 67663, Kaiserslautern, Germany. goossen@chemie.uni-kl.de.
Lukas J
0000-0002-2547-3037
LJ
Gooßen
C−H activation; alkynes; decarboxylation; ruthenium; synthetic methods