Short Step Synthesis of 4-Substituted Indoles Using Palladium-catalyzed C-C Bond Forming Reaction

Heterocycles ◽  
1996 ◽  
Vol 42 (1) ◽  
pp. 113 ◽  
Author(s):  
Miwako Mori ◽  
Kazuyuki Doi
Keyword(s):  
Bond Forming ◽  
Palladium Catalyzed

ChemInform Abstract: Me3(OMe)tBuXPhos: A Surrogate Ligand for Me4tBuXPhos in Palladium-Catalyzed C-N and C-O Bond-Forming Reactions.

ChemInform ◽  
2012 ◽  
Vol 43 (27) ◽  
pp. no-no
Author(s):  
Satoshi Ueda ◽  
Siraj Ali ◽  
Brett P. Fors ◽  
Stephen L. Buchwald
Keyword(s):  
Bond Forming ◽  
Bond Forming Reactions ◽  
Palladium Catalyzed

scholarly journals Iodination of carbohydrate-derived 1,2-oxazines to enantiopure 5-iodo-3,6-dihydro-2H-1,2-oxazines and subsequent palladium-catalyzed cross-coupling reactions

2016 ◽  
Vol 12 ◽  
pp. 2898-2905 ◽  
Author(s):  
Michal Medvecký ◽  
Igor Linder ◽  
Luise Schefzig ◽  
Hans-Ulrich Reissig ◽  
Reinhold Zimmer
Keyword(s):  
Click Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
High Efficacy ◽  
Carbon Bond ◽  
Bond Forming ◽  
Cross Coupling Reactions ◽  
Carbon Carbon Bond ◽  
Palladium Catalyzed ◽  
Oxazine Derivatives

Iodination of carbohydrate-derived 3,6-dihydro-2H-1,2-oxazines of type 3 using iodine and pyridine in DMF furnished 5-iodo-substituted 1,2-oxazine derivatives 4 with high efficacy. The alkenyl iodide moiety of 1,2-oxazine derivatives syn-4 and anti-4 was subsequently exploited for the introduction of new functionalities at the C-5 position by applying palladium-catalyzed carbon–carbon bond-forming reactions such as Sonogashira, Heck, or Suzuki coupling reactions as well as a cyanation reaction. These cross-coupling reactions led to a series of 5-alkynyl-, 5-alkenyl-, 5-aryl- and 5-cyano-substituted 1,2-oxazine derivatives being of considerable interest for further synthetic elaborations. This was exemplarily demonstrated by the hydrogenation of syn-21 and anti-24 and by a click reaction of a 5-alkynyl-substituted precursor.

scholarly journals Palladium(II)-Catalyzed C(sp3)–H Activation of N,O-Ketals towards a Method for the β-Functionalization of Ketones

Synlett ◽  
2019 ◽  
Vol 30 (04) ◽  
pp. 454-458 ◽  
Author(s):  
Danny Ho ◽  
Jonas Calleja ◽  
Matthew Gaunt
Keyword(s):  
Carboxylic Acids ◽  
Functional Groups ◽  
Building Blocks ◽  
Activation Pathway ◽  
Bond Forming ◽  
Aliphatic Ketones ◽  
Palladium Catalyzed

A method for the formal β-functionalization of aliphatic ketones via a palladium-catalyzed sp3 C–H activation pathway is reported. An N,O-ketal directs an aliphatic C–H carbonylation to form γ-lactams which upon hydrolysis generate γ-keto carboxylic acids. This C–C bond-forming reaction is tolerant of a range of functional groups, enabling the synthesis of a range of synthetically important building blocks. Furthermore, the concepts underlying this transformation have also enabled the development of a related C–H alkenylation process to highly functionalised heterocycles.

Post-synthetic methods for functionalization of imidazole-fused porphyrins

2018 ◽  
Vol 22 (08) ◽  
pp. 619-631 ◽  
Author(s):  
Inna A. Abdulaeva ◽  
Kirill P. Birin ◽  
Yulia G. Gorbunova ◽  
Aslan Yu. Tsivadze ◽  
Alla Bessmertnykh-Lemeune
Keyword(s):  
Aromatic Aldehyde ◽  
Synthetic Methods ◽  
Synthetic Approach ◽  
Synthetic Route ◽  
Bond Forming ◽  
The Core ◽  
Material Chemistry ◽  
Bond Forming Reactions ◽  
Palladium Catalyzed

Several methods for the post-synthetic modification of imidazo[4,5-[Formula: see text]]porphyrins are reported. First, a synthetic approach to the isomeric difunctionalized porphyrins, containing two [Formula: see text]-fused 2-aryl-1[Formula: see text]-imidazole cycles at adjacent or opposite pyrrole rings of the macrocycle is developed. The core chemistry of this synthetic route is the transformation of 2-aryl-1[Formula: see text]-imidazo[4,5-[Formula: see text]]porphyrins into corresponding imidazodioxochlorins followed by Debus–Radziszewski condensation with aromatic aldehyde. Next, 2-(4-bromophenyl)-1[Formula: see text]-imidazo[4,5-[Formula: see text]]-5,10,15,20-tetramesitylporphyrin was transformed into useful carboxy- and phosphonato-substituted precursors for material chemistry according to palladium-catalyzed C–C and C–P bond forming reactions.

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