Premium
Triarylborane‐Catalyzed Alkenylation Reactions of Aryl Esters with Diazo Compounds
Author(s) -
Dasgupta Ayan,
Stefkova Katarína,
Babaahmadi Rasool,
Gierlichs Lukas,
Ariafard Alireza,
Melen Rebecca L.
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202007176
Subject(s) - diazo , chemistry , catalysis , borane , aryl , combinatorial chemistry , enyne , medicinal chemistry , tris , metal , organic chemistry , biochemistry , alkyl
Herein we report a facile, mild reaction protocol to form carbon–carbon bonds in the absence of transition metal catalysts. We demonstrate the metal‐free alkenylation reactions of aryl esters with α‐diazoesters to give highly functionalized enyne products. Catalytic amounts of tris(pentafluorophenyl)borane (10–20 mol %) are employed to afford the C=C coupled products (31 examples) in good to excellent yields (36–87 %). DFT studies were used to elucidate the mechanism for this alkenylation reaction.