Cp-Free Cobalt-Catalyzed C–H Activation/Annulations by Traceless N,O‑Bidentate Directing Group: Access to Isoquinolines

N,O-Bidentate directing-enabled, traceless heterocycle synthesis is described via Cp*-free cobalt-catalyzed C–H activation/annulation. The weakly coordinating nature of the carboxylic acid was employed for the preparation of isoquinolines. Meanwhile, the N–O bond of the α-imino-oxy acid can serve as...

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Bibliographic Details
Published inOrganic letters Vol. 21; no. 8; pp. 2863 - 2866
Main Authors Li, Xiao-Cai, Du, Cong, Zhang, He, Niu, Jun-Long, Song, Mao-Ping
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.04.2019
Amer Chemical Soc
Subjects
alkynes
carbon-hydrogen bond activation
carboxylic acids
chemical bonding
chemical reactions
chemical structure
Chemistry
Chemistry, Organic
isoquinolines
oxidants
Physical Sciences
Science & Technology
FUNCTIONALIZATION
MILD
SUBSTITUTED ISOQUINOLINES
4+2 ANNULATION
O BOND
IMINES
BOND FORMATION
C(SP)-H
ALKYNES
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Summary:N,O-Bidentate directing-enabled, traceless heterocycle synthesis is described via Cp*-free cobalt-catalyzed C–H activation/annulation. The weakly coordinating nature of the carboxylic acid was employed for the preparation of isoquinolines. Meanwhile, the N–O bond of the α-imino-oxy acid can serve as an internal oxidant. Terminal as well as internal alkynes can be efficiently applied to the catalytic system. This operationally simple approach shows a broad substrate scope with the products obtained in good to excellent yields.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.9b00866