Pd(II)/Cu(II)-Catalyzed Regio- and Stereoselective Synthesis of (E)‑3-Arylmethyleneisoindolin-1-ones Using Air as the Terminal Oxidant

Regio- and stereoselective synthesis of (E)-3-arylmethyleneisoindolin-1-ones via Pd­(II)/Cu­(II)-catalyzed one-pot C–C/C–N bond forming sequence between amides and styrenes is reported. This method provides facile and rapid access to a diverse range of such compounds using readily available starting...

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Published inOrganic letters Vol. 20; no. 24; pp. 7869 - 7874
Main Authors Youn, So Won, Ko, Tae Yun, Kim, Young Ho, Kim, Yun Ah
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.12.2018
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALIPHATIC AMIDES
OXIDATIVE OLEFINATION
INTRAMOLECULAR CYCLIZATION
POSSESSING INHIBITORY-ACTIVITY
ONE-POT SYNTHESIS
MIYAURA DOMINO REACTIONS
HIGHLY REGIO
CATALYZED ANNULATION
REGIOSELECTIVE SYNTHESIS
C-H ACTIVATION
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Summary:Regio- and stereoselective synthesis of (E)-3-arylmethyleneisoindolin-1-ones via Pd­(II)/Cu­(II)-catalyzed one-pot C–C/C–N bond forming sequence between amides and styrenes is reported. This method provides facile and rapid access to a diverse range of such compounds using readily available starting materials under mild aerobic conditions with good functional group tolerance and high selectivity and efficiency. Further elaboration of the products obtained from this process enabled very short and efficient syntheses of aristolactam and indoloisoquinolinone alkaloids.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b03409