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Formations of aryl or pyrrole ring via palladium‐catalyzed CH functionalization on amido‐substituted quinones in the presence of amines or phosphines
Author(s) -
Li CangSian,
Tseng YiPing,
Hsu TingHsuan,
Chang ChiaoYun,
Hong FungE
Publication year - 2021
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.202000375
Subject(s) - chemistry , moiety , pyrrole , palladium , furan , ring (chemistry) , medicinal chemistry , aryl , tertiary amine , quinone , catalysis , polymer chemistry , organic chemistry , alkyl
A di‐substituted quinone ( 5 ), having two amido‐groups at opposite positions, was reacted with tertiary, secondary, or primary amines via a one‐pot reaction in the presence of palladium salt. Crystal structures of some of the products, 7b ‐ 7c , from these reactions reveal that two new pyrrole rings are formed and linked to quinone framework of 5 by taking advantage of the in situ generated alkenyl moiety, which is from the reaction of amine with palladium salt. Furthermore, the reaction of di‐amido substituted diquinone ( 8a ) with tertiary amines led to the formations of 9a ‐ 9d with new pyrrole and benzene rings to the moiety of 8a . Similar procedures for the reaction of 8b with tertiary amines provides an alternated route to make notable 1,4,5,8‐phenanthrenetetraone derivatives, 9e and 9f . Moreover, the reaction of diquinone ( 8a ) with tricyclohexylphosphine led to two products, 11 and 13 , with new formation of furan ring as well as PC bond. Further reaction of 11 with NBu 3 yielded 14 with newly formed pyrrole ring. Crystal structures of these newly‐formed compounds revealed by single‐crystal X‐ray diffraction methods substantiate the claim.