ChemInform Abstract: Palladium-Catalyzed Vinylic Substitution of Aryl/Vinyl Iodides and Triflates with α-Methylene-γ-butyrolactone - An Application to the Synthesis of 3-Alkyl-γ-butyrolactones Through Combined Palladium-Catalyzed Coupling/Hydrogenation Re

ChemInform ◽  
2010 ◽  
Vol 33 (13) ◽  
pp. no-no
Author(s):  
Antonio Arcadi ◽  
Marco Chiarini ◽  
Fabio Marinelli ◽  
Zoltan Berente ◽  
Laszlo Kollar
Keyword(s):  
Palladium Catalyzed ◽  
Vinylic Substitution ◽  
Vinyl Iodides

Stereospecific, Palladium-catalyzed C(sp3)–H Alkenylation and Alkynylation of a Proline Derivative Enabled by 8-Aminoquinoline as a Directing Group

2020 ◽  
Author(s):  
Aleksandra Balliu ◽  
Aaltje Roelofje Femmigje Strijker ◽  
Michael Oschmann ◽  
Monireh Pourghasemi Lati ◽  
Oscar Verho
Keyword(s):  
Carboxylic Acid ◽  
Building Blocks ◽  
Wide Range ◽  
Palladium Catalyzed ◽  
Directing Group ◽  
High Yields ◽  
Vinyl Iodides ◽  
Initial Results

<p>In this preprint, we present our initial results concerning a stereospecific Pd-catalyzed protocol for the C3 alkenylation and alkynylation of a proline derivative carrying the well utilized 8‑aminoquinoline directing group. Efficient C–H alkenylation was achieved with a wide range of vinyl iodides bearing different aliphatic, aromatic and heteroaromatic substituents, to furnish the corresponding C3 alkenylated products in good to high yields. In addition, we were able show that this protocol can also be used to install an alkynyl group into the pyrrolidine scaffold, when a TIPS-protected alkynyl bromide was used as the reaction partner. Furthermore, two different methods for the removal of the 8-aminoquinoline auxiliary are reported, which can enable access to both <i>cis</i>- and <i>trans</i>-configured carboxylic acid building blocks from the C–H alkenylation products.</p>

Palladium-Catalyzed Coupling of (1,3-Butadiynyl)amines with Aryl and Vinyl Iodides

Synthesis ◽  
1991 ◽  
Vol 1991 (03) ◽  
pp. 232-233 ◽  
Author(s):  
Achim Löffler ◽  
Gerhard Himbert
Keyword(s):  
Palladium Catalyzed ◽  
Vinyl Iodides

Palladium-catalyzed cross-coupling of vinyl iodides with organostannanes: synthesis of unsymmetrical divinyl ketones

1984 ◽  
Vol 106 (21) ◽  
pp. 6417-6422 ◽  
Author(s):  
W. F. Goure ◽  
Michael E. Wright ◽  
P. D. Davis ◽  
Sharada S. Labadie ◽  
J. K. Stille
Keyword(s):  
Cross Coupling ◽  
Palladium Catalyzed ◽  
Vinyl Iodides
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