Oxidative Annulation of Acetanilides with Alkynes Catalyzed by Cyclopentadienyl Rhodium(III) Complexes with Pendant Amides

It has been established that a cationic cyclopentadienyl (Cp) rhodium(III) complex with a pendant N-phenylcarbamoyl moiety ((CpRhIII)-Rh-A1) showed high catalytic activity towards the oxidative [3+2] annulation of acetanilides with internal alkynes to produce substituted indoles. Catalytic activity...

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Bibliographic Details
Published inAsian journal of organic chemistry Vol. 8; no. 7; pp. 986 - 993
Main Authors Yoshimura, Ryo, Shibata, Yu, Yoshizaki, Soichi, Terasawa, Jyunichi, Yamada, Takayuki, Tanaka, Ken
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.07.2019
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
C-H Functionalization
(ELECTRON-DEFICIENT ETA-CYCLOPENTADIENYL)RHODIUM(III) CATALYST
ANILIDES
C-H ACTIVATION
FUNCTIONALIZATION
Cyclopentadienyl Complexes
ALKENES
CYCLOADDITION
Rhodium
ACRYLIC-ACIDS
LIGANDS
INDOLE
Indoles
Annulation
BENZOIC-ACIDS
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Summary:It has been established that a cationic cyclopentadienyl (Cp) rhodium(III) complex with a pendant N-phenylcarbamoyl moiety ((CpRhIII)-Rh-A1) showed high catalytic activity towards the oxidative [3+2] annulation of acetanilides with internal alkynes to produce substituted indoles. Catalytic activity of the (CpRhIII)-Rh-A1 complex in the reactions of symmetric internal alkynes (diphenylacetylene and 6-dodecyne) was higher than that of the Cp*-rhodium(III) complex and comparable to that of a Cp-rhodium(III) complex with two ethoxycarbonyl groups ((CpRhIII)-Rh-E). On the other hand, the (CpRhIII)-Rh-A1 complex showed significantly higher catalytic activity than the (CpRhIII)-Rh-E complex in the reactions of unsymmetric internal alkynes (1-phenyl-1-propyne and 1-phenyl-1-hexyne). Additionally, the catalytic activity of the (CpRhIII)-Rh-A1 complex in the oxidative tandem [2+2+2] annulation-lactamization of acetanilides with two unsymmetric electron-deficient internal alkynes (ethtyl 2-butynoate) was also comparable to that of the (CpRhIII)-Rh-E complex.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.201900139