A Facile Regiocontrol in the Palladium-Catalyzed Annulation of Fluorine-Containing Internal Alkynes with Variously Substituted 2-Iodoanilines:  A New Regioselective Synthesis of 2- or 3-Fluoroalkylated Indole Derivatives

2004 ◽  
Vol 69 (24) ◽  
pp. 8258-8265 ◽  
Author(s):  
Tsutomu Konno ◽  
Jungha Chae ◽  
Takashi Ishihara ◽  
Hiroki Yamanaka
Keyword(s):  
Regioselective Synthesis ◽  
Indole Derivatives ◽  
Internal Alkynes ◽  
Palladium Catalyzed

scholarly journals Regioselective Synthesis of Substituted Pyrroles: Efficient Palladium-Catalyzed Cyclization of Internal Alkynes and 2-Amino-3-iodoacrylate Derivatives.

ChemInform ◽  
2007 ◽  
Vol 38 (15) ◽  
Author(s):  
Matthew L. Crawley ◽  
Igor Goljer ◽  
Douglas J. Jenkins ◽  
John F. Mehlmann ◽  
Lisa Nogle ◽  
...  
Keyword(s):  
Regioselective Synthesis ◽  
Internal Alkynes ◽  
Palladium Catalyzed ◽  
Substituted Pyrroles

Regioselective Synthesis of Substituted Pyrroles:  Efficient Palladium-Catalyzed Cyclization of Internal Alkynes and 2-Amino-3-iodoacrylate Derivatives

2006 ◽  
Vol 8 (25) ◽  
pp. 5837-5840 ◽  
Author(s):  
Matthew L. Crawley ◽  
Igor Goljer ◽  
Douglas J. Jenkins ◽  
John F. Mehlmann ◽  
Lisa Nogle ◽  
...  
Keyword(s):  
Regioselective Synthesis ◽  
Internal Alkynes ◽  
Palladium Catalyzed ◽  
Substituted Pyrroles

A Facile Synthesis of Various Fluorine-Containing Indole Derivatives via Palladium-Catalyzed Annulation of Internal Alkynes

2004 ◽  
Vol 33 (3) ◽  
pp. 314-315 ◽  
Author(s):  
Jungha Chae ◽  
Tsutomu Konno ◽  
Takashi Ishihara ◽  
Hiroki Yamanaka
Keyword(s):  
Indole Derivatives ◽  
Facile Synthesis ◽  
Internal Alkynes ◽  
Palladium Catalyzed

scholarly journals Divergent Synthesis of Indolenine and Indoline Ring Systems by Palladium-Catalyzed Asymmetric Dearomatization of Indoles

2021 ◽  
Author(s):  
Dong Gao ◽  
Lei Jiao
Keyword(s):  
Biologically Active ◽  
Indole Derivatives ◽  
Reaction Sequence ◽  
High Demand ◽  
Internal Alkynes ◽  
Palladium Catalyzed ◽  
Efficient Construction ◽  
Acidic Conditions ◽  
Semipinacol Rearrangement ◽  
Quaternary Stereocenter

Dearomatized indole derivatives bearing a C3- or C2-stereocenter exist ubiquitously in natural products and biologically active molecules. Despite remarkable advances in their chemical synthesis, stereoselective and regio-divergent methods are still in a high demand. Herein, a Pd-catalyzed intermolecular asymmetric spiroannulation of 2,3-disubstituted indoles with internal alkynes has been developed for the efficient construction of indoline structures with a C2-quaternary stereocenter. Stereospecific aza-semipinacol rearrangement of these indoline derivatives under acidic conditions afforded indolenine products bearing a C3-quaternary stereocenter, where the selectivity for the rearranging group could be controlled by the reaction sequence. The asymmetric spiroannulation together with the subsequent aza-semipinacol rearrangement enabled a divergent access to dearomatized indole derivatives with either a C3- or a C2-quaternary stereocenter.

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