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Tandem C( sp 3 )−H Arylation/Oxidation and Arylation/Allylic Substitution of Isoindolinones
Author(s) -
Jiménez Jacqueline,
Kim ByeongSeon,
Walsh Patrick J.
Publication year - 2016
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.201600654
Subject(s) - chemistry , allylic rearrangement , tandem , catalysis , combinatorial chemistry , aryl , functional group , tsuji–trost reaction , palladium , alkylation , leaving group , organic chemistry , materials science , alkyl , polymer , composite material
Isoindolinones comprise an important class of medicinally active compounds. Herein we report a straightforward functionalization of isoindolinones with aryl bromides (22 examples) using a palladium(II) acetate/NIXANTPHOS‐based catalyst system. Additionally 3‐aryl‐3‐hydroxyisoindolinone derivatives, which exhibit anti‐tumor activity, can be accessed via a tandem reaction. Thus, when the arylation product is exposed to air under basic conditions, in situ oxidation takes place to install the 3‐hydroxy group. Furthermore, a tandem arylation/allylic substitution reaction is advanced in which both the arylation and allylic substitution are catalyzed by the same palladium catalyst. Finally, a tandem arylation/alkylation procedure is presented. These tandem reactions enable the synthesis of a variety of structurally diverse isoindolinone derivatives from common starting materials.