TY - JOUR
T1 - Selective Palladium-Catalyzed Carbonylation of Alkynes
T2 - An Atom-Economic Synthesis of 1,4-Dicarboxylic Acid Diesters
AU - Liu, Jiawang
AU - Dong, Kaiwu
AU - Franke, Robert
AU - Neumann, Helfried
AU - Jackstell, Ralf
AU - Beller, Matthias
N1 - Publisher Copyright:
© 2018 American Chemical Society.
PY - 2018/8/15
Y1 - 2018/8/15
N2 - A class of novel diphosphine ligands bearing pyridine substituents was designed and synthesized for the first time. The resulting palladium complexes of L1 allow for chemo- and regioselective dialkoxycarbonylation of various aromatic and aliphatic alkynes affording a wide range of 1,4-dicarboxylic acid diesters in high yields and selectivities. Kinetic studies suggest the generation of 1,4-dicarboxylic acid diesters via cascade hydroesterification of the corresponding alkynes. Based on these investigations, the chemo- and regioselectivities of alkyne carbonylations can be controlled as shown by switching the ligand from L1 to L3 or L9 to give α,β-unsaturated esters.
AB - A class of novel diphosphine ligands bearing pyridine substituents was designed and synthesized for the first time. The resulting palladium complexes of L1 allow for chemo- and regioselective dialkoxycarbonylation of various aromatic and aliphatic alkynes affording a wide range of 1,4-dicarboxylic acid diesters in high yields and selectivities. Kinetic studies suggest the generation of 1,4-dicarboxylic acid diesters via cascade hydroesterification of the corresponding alkynes. Based on these investigations, the chemo- and regioselectivities of alkyne carbonylations can be controlled as shown by switching the ligand from L1 to L3 or L9 to give α,β-unsaturated esters.
UR - https://www.scopus.com/pages/publications/85050769084
U2 - 10.1021/jacs.8b05852
DO - 10.1021/jacs.8b05852
M3 - 文章
C2 - 30032618
AN - SCOPUS:85050769084
SN - 0002-7863
VL - 140
SP - 10282
EP - 10288
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 32
ER -