Palladium-Catalyzed Regioselective Aromatic Extension of Internal Alkynes through a Norbornene-Controlled Reaction Sequence

2018 ◽  
Vol 130 (13) ◽  
pp. 3439-3443 ◽  
Author(s):  
Qingyang Zhao ◽  
Wai Chung Fu ◽  
Fuk Yee Kwong
Keyword(s):  
Reaction Sequence ◽  
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.

A New Reaction Sequence Involving Palladium-Catalyzed Unsymmetrical Aryl Coupling

2004 ◽  
Vol 126 (1) ◽  
pp. 78-79 ◽  
Author(s):  
Fiorenza Faccini ◽  
Elena Motti ◽  
Marta Catellani
Keyword(s):  
Reaction Sequence ◽  
Palladium Catalyzed

Palladium-catalyzed carbonylative synthesis of substituted cyclopentenones from aryl iodides and internal alkynes

2019 ◽  
Vol 17 (24) ◽  
pp. 5882-5885 ◽  
Author(s):  
Jin-Bao Peng ◽  
Wei-Feng Wang ◽  
Xiao-Feng Wu
Keyword(s):  
Aryl Iodides ◽  
Internal Alkynes ◽  
Palladium Catalyzed

In this Communication, a palladium-catalyzed carbonylative synthesis of substituted cyclopentenones has been developed.

Synthesis of α-pyrones via palladium-catalyzed annulation of internal alkynes

1998 ◽  
Vol 39 (32) ◽  
pp. 5713-5716 ◽  
Author(s):  
Richard C. Larock ◽  
Xiaojun Han ◽  
Mark J. Doty
Keyword(s):  
Internal Alkynes ◽  
Palladium Catalyzed
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