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Pot‐Economical Synthesis of Hydroxylated Arylethenyl‐arylethynyl‐arenes through Sequential Decarboxylative Perkin–Sonogashira Reactions
Author(s) -
Shard Amit,
Kumar Rajesh,
Equbal Danish,
Sinha Arun Kumar
Publication year - 2018
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201700504
Subject(s) - sonogashira coupling , chemistry , decarboxylation , combinatorial chemistry , alicyclic compound , conjugated system , organic chemistry , palladium , catalysis , polymer
A simple, economical and one‐pot protocol is developed for construction of multiple carbon–carbon bonds having C(sp 2 )−C(sp 2 ) and C(sp 2 )−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 (C 6 –C 1 unit), halo‐phenylacetic acids (C 6 –C 2 unit) and arylacetylenes (C 6 –C 3 unit) resulting in the formation of highly π‐conjugated complex arylethenyl‐arylethynyl‐arenes (C 6 –C 2 –C 6 –C 2 –C 6 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 CO 2 and H 2 O 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.