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Palladium‐Catalyzed Synthesis of 2,3‐Disubstituted Benzofurans: An Approach Towards the Synthesis of Deuterium Labeled Compounds
Author(s) -
Agasti Soumitra,
Maity Soham,
Szabo Kalman J.,
Maiti Debabrata
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500308
Subject(s) - chemistry , regioselectivity , benzofuran , palladium , phenol , catalysis , alkyl , phenols , methylene , organic chemistry , conjugated system , combinatorial chemistry , polymer
Palladium‐catalyzed oxidative annulations between phenols and alkenylcarboxylic acids produced a library of benzofuran compounds. Depending on the nature of the substitution of the phenol precursor, either 2,3‐dialkylbenzofurans or 2‐alkyl‐3‐methylene‐2,3‐dihydrobenzofurans can be synthesized with excellent regioselectivity. Reactions between conjugated 5‐phenylpenta‐2,4‐dienoic acids and phenol gave 3‐alkylidenedihydrobenzofuran alkaloid motifs while biologically active 7‐arylbenzofuran derivatives were prepared by starting from 2‐phenylphenols. More interestingly, selective incorporation of deuterium from D 2 O has been discovered, which offers an attractive one‐step method to access deuterated compounds.