Premium
Pd‐Catalyzed Orthogonal Knoevenagel/Perkin Condensation–Decarboxylation–Heck/Suzuki Sequences: Tandem Transformations of Benzaldehydes into Hydroxy‐Functionalized Antidiabetic Stilbene–Cinnamoyl Hybrids and Asymmetric Distyrylbenzenes
Author(s) -
Sharma Naina,
Sharma Abhishek,
Shard Amit,
Kumar Rakesh,
Sinha Arun K.
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201101174
Subject(s) - knoevenagel condensation , decarboxylation , chemistry , cinnamic acid , heck reaction , tandem , organic chemistry , catalysis , combinatorial chemistry , palladium , materials science , composite material
Tandem reactions that involve chemoselective Knoevenagel/Perkin condensation–decarboxylation–Heck/Suzuki coupling or Heck–aldol sequences have been achieved. This enabled the first concise and efficient synthesis of several important hydroxy‐functionalized compound classes, such as stilbene–cinnamoyl hybrids (potent protein tyrosine phosphatase1B inhibitors), cinnamoyl–cinnamic acid hybrids, asymmetric distyrylbenzenes, and biarylstyrenes. Previously reported synthesis require multiple steps and protection/deprotection manipulations.