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Palladium‐Catalyzed Formal [4+2] Cycloaddition of Benzoic and Acrylic Acids with 1,3‐Dienes via C—H Bond Activation: Efficient Access to 3,4‐Dihydroisocoumarin and 5,6‐Dihydrocoumalins
Author(s) -
Sun Youwen,
Zhang Guozhu
Publication year - 2018
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201800149
Subject(s) - chemistry , cycloaddition , palladium , annulation , catalysis , isoprene , benzoic acid , formal synthesis , medicinal chemistry , bond cleavage , natural product , organic chemistry , combinatorial chemistry , stereochemistry , copolymer , polymer
We report a palladium‐catalyzed formal intermolecular [4+2] cycloaddition of benzoic and acrylic acids with 1,3‐dienes including the stock chemicals 1,3‐butadiene and isoprene leading to synthetically useful 3,4‐dihydroisocoumarins and 5,6‐dihydrocoumalins. Stepwise C—H bond cleavage and annulation are likely involved in the reaction pathway. The synthetic potential of the methodology was demonstrated by two short derivatizations and total synthesis of natural product Clausamine B.