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- Title
Pot‐Economical Synthesis of Hydroxylated Arylethenyl‐arylethynyl‐arenes through Sequential Decarboxylative Perkin–Sonogashira Reactions.
- Authors
Shard, Amit; Kumar, Rajesh; Equbal, Danish; Sinha, Arun Kumar
- Abstract
Abstract: A simple, economical and one‐pot protocol is developed for construction of multiple carbon–carbon bonds having C(sp2)−C(sp2) and C(sp2)−C(sp) hybridization, as these intriguing molecular architectures exhibit significant optoelectronic and medicinal properties. To this end, a sequential reaction is devised that allows one‐pot three‐component reactions of hydroxybenzaldehydes (C6–C1 unit), halo‐phenylacetic acids (C6–C2 unit) and arylacetylenes (C6–C3 unit) resulting in the formation of highly π‐conjugated complex arylethenyl‐arylethynyl‐arenes (C6–C2–C6–C2–C6 unit) bearing a hydroxy group via sequential Perkin condensation–decarboxylation–Sonogashira coupling in polyethylene glycol with microwave irradiation. The process avoids protection–deprotection manipulations, generates CO2 and H2O as by‐products and is successfully extended for the efficient construction of a wide series of novel aliphatic/alicyclic/(hetero)aromatic arylethenyl‐arylethynyl‐arenes with pendant hydroxy functionality, which could undergo further chemical modification to achieve target biological and physical properties.
- Subjects
CARBON; OPTOELECTRONIC devices; MOLECULES
- Publication
Asian Journal of Organic Chemistry, 2018, Vol 7, Issue 1, p189
- ISSN
2193-5807
- Publication type
Article
- DOI
10.1002/ajoc.201700504