Pd-Catalyzed Orthogonal Knoevenagel/Perkin Condensation-Decarboxylation-Heck/Suzuki Sequences: Tandem Transformations of Benzaldehydes into Hydroxy-Functionalized Antidiabetic Stilbene-Cinnamoyl Hybrids and Asymmetric Distyrylbenzenes

• Published in: Chemistry : a European journal Vol. 17; no. 37; pp. 10350 - 10356
• Main Authors: Sharma, Naina, Sharma , Abhishek, Shard, Amit, Kumar, Rakesh, Saima, Sinha, Arun K.
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 05.09.2011; WILEY‐VCH Verlag; Wiley; Wiley Subscription Services, Inc
• Subjects: Benzaldehydes - chemistry; Catalysis; Chemistry; Chemistry, Multidisciplinary; Cinnamates - chemical synthesis; Cinnamates - chemistry; Cinnamates - pharmacology; Combinatorial Chemistry Techniques; Condensation; CC coupling; Decarboxylation; Hypoglycemic Agents - chemical synthesis; Hypoglycemic Agents - chemistry; Hypoglycemic Agents - pharmacology; Molecular Structure; olefination; palladium; Palladium - chemistry; Physical Sciences; Science & Technology; Stilbenes - chemical synthesis; Stilbenes - chemistry; Stilbenes - pharmacology; stilbenoids; C-C coupling; ORGANIC-SYNTHESIS; stilbenoids; BIS-STYRYLBENZENES; HECK; ACIDS; SUBSTITUTED BENZALDEHYDES; MULTICOMPONENT REACTIONS; COUPLING REACTIONS; condensation; CHEMISTRY; palladium; METAL; BINDING LIGANDS; olefination
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201101174

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. Condense and couple: Tandem reactions that involve chemoselective condensation–decarboxylation–coupling or Heck–aldol sequences have been achieved. These enable concise and efficient synthesis of stilbene–cinnamoyl hybrids, cinnamoyl–cinnamic acid hybrids, asymmetric hydroxy‐distyrylbenzenes, and hydroxylated biarylstyrenes (see scheme).