One‐Pot Synthesis of Polysubstituted Indoles via the Indium‐Promoted Regioselective Hydrohydrazination of Terminal Alkynes
Abstract: We demonstrated that indium bromide, a trivalent indium compound with strong tolerance toward various coordination functional groups, can be used as a sole promotor to effectively promote the hydrohydrazination of a variety of N‐phenylhydrazines with aromatic/aliphatic alkynes and the subsequent [3,3]‐sigmatropic reaction of the hydrazone intermediate, leading to the one‐pot preparation of various poly‐substituted indole derivatives. Notably, the initial hydrohydrazination proceeded in a Markovnikov‐type manner and showed high regioselectivity, with the hydrohydrazination of arylalkynes affording only 2‐arylindole derivatives. Therefore, our findings provide a facile and practical one‐pot process for the synthesis of polysubstituted indole derivatives from various phenylhydrazines and aromatic/aliphatic alkynes using only one promotor.
- Location
-
Deutsche Nationalbibliothek Frankfurt am Main
- Extent
-
Online-Ressource
- Language
-
Englisch
- Bibliographic citation
-
One‐Pot Synthesis of Polysubstituted Indoles via the Indium‐Promoted Regioselective Hydrohydrazination of Terminal Alkynes ; day:15 ; month:01 ; year:2025 ; extent:7
Asian journal of organic chemistry ; (15.01.2025) (gesamt 7)
- Creator
-
Sakai, Norio
Yokoyama, Takahiro
Ishida, Kento
- DOI
-
10.1002/ajoc.202400682
- URN
-
urn:nbn:de:101:1-2501161315283.704572675608
- Rights
-
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
-
15.08.2025, 7:22 AM CEST
Data provider
This object is provided by:
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Sakai, Norio
- Yokoyama, Takahiro
- Ishida, Kento
Other Objects (12)
Catalytic regioselective hydroamination of alkenes and alkynes
Regioselective trans ‐Hydrostannation of Boron‐Capped Alkynes
Unbiased C3‐Electrophilic Indoles: Triflic Acid Mediated C3‐Regioselective Hydroarylation of N−H Indoles **
Unbiased C3‐Electrophilic Indoles: Triflic Acid Mediated C3‐Regioselective Hydroarylation of N−H Indoles **
An Operationally Simple, Regioselective, Platinum‐Catalyzed Hydroboration of Unactivated Alkynes
Regioselective and Enantioselective Copper‐Catalyzed Hydroaminocarbonylation of Unactivated Alkenes and Alkynes
Regioselective and Enantioselective Copper‐Catalyzed Hydroaminocarbonylation of Unactivated Alkenes and Alkynes
One‐Pot Regioselective γ‐Trifluoromethylthiolation and γ‐Methylthiolation of Enals
Silica: An efficient catalyst for one-pot regioselective synthesis of dithioethers
Zirconoarylation of alkynes through p-chloranil-promoted reductive elimination of arylzirconates
Regioselective, One-Pot Syntheses of Symmetrically and Unsymmetrically Halogenated 2′,6′-Bispyrazolylpyridines
Regioselective Hydroalkylation and Arylalkylation of Alkynes by Photoredox/Nickel Dual Catalysis: Application and Mechanism
Catalytic regioselective hydroamination of alkenes and alkynes
Regioselective trans ‐Hydrostannation of Boron‐Capped Alkynes
Unbiased C3‐Electrophilic Indoles: Triflic Acid Mediated C3‐Regioselective Hydroarylation of N−H Indoles **
Unbiased C3‐Electrophilic Indoles: Triflic Acid Mediated C3‐Regioselective Hydroarylation of N−H Indoles **
An Operationally Simple, Regioselective, Platinum‐Catalyzed Hydroboration of Unactivated Alkynes
Regioselective and Enantioselective Copper‐Catalyzed Hydroaminocarbonylation of Unactivated Alkenes and Alkynes
Regioselective and Enantioselective Copper‐Catalyzed Hydroaminocarbonylation of Unactivated Alkenes and Alkynes
One‐Pot Regioselective γ‐Trifluoromethylthiolation and γ‐Methylthiolation of Enals
Silica: An efficient catalyst for one-pot regioselective synthesis of dithioethers
Zirconoarylation of alkynes through p-chloranil-promoted reductive elimination of arylzirconates
Regioselective, One-Pot Syntheses of Symmetrically and Unsymmetrically Halogenated 2′,6′-Bispyrazolylpyridines
Regioselective Hydroalkylation and Arylalkylation of Alkynes by Photoredox/Nickel Dual Catalysis: Application and Mechanism
Catalytic regioselective hydroamination of alkenes and alkynes
Regioselective trans ‐Hydrostannation of Boron‐Capped Alkynes
Unbiased C3‐Electrophilic Indoles: Triflic Acid Mediated C3‐Regioselective Hydroarylation of N−H Indoles **
Unbiased C3‐Electrophilic Indoles: Triflic Acid Mediated C3‐Regioselective Hydroarylation of N−H Indoles **
An Operationally Simple, Regioselective, Platinum‐Catalyzed Hydroboration of Unactivated Alkynes
Regioselective and Enantioselective Copper‐Catalyzed Hydroaminocarbonylation of Unactivated Alkenes and Alkynes
Regioselective and Enantioselective Copper‐Catalyzed Hydroaminocarbonylation of Unactivated Alkenes and Alkynes
One‐Pot Regioselective γ‐Trifluoromethylthiolation and γ‐Methylthiolation of Enals
Silica: An efficient catalyst for one-pot regioselective synthesis of dithioethers
Zirconoarylation of alkynes through p-chloranil-promoted reductive elimination of arylzirconates
Regioselective, One-Pot Syntheses of Symmetrically and Unsymmetrically Halogenated 2′,6′-Bispyrazolylpyridines