Synthesis of 3-(Diarylmethylenyl)oxindole by a Palladium-Catalyzed Domino Carbopalladation/C−H Activation/C−C Bond-Forming Process

2006 ◽  
Vol 8 (21) ◽  
pp. 4927-4930 ◽  
Author(s):  
Artur Pinto ◽  
Luc Neuville ◽  
Pascal Retailleau ◽  
Jieping Zhu
Keyword(s):  
Forming Process ◽  
Bond Forming ◽  
Palladium Catalyzed

Nickel-Catalyzed Electronically-Reversed Enantioselective Hydrocarbofunctionalizations of Acrylamides

Synlett ◽  
2021 ◽  
Author(s):  
Lou Shi ◽  
Wei Shu
Keyword(s):  
Nickel Catalyst ◽  
Functional Group ◽  
Optically Active ◽  
Forming Process ◽  
Carbon Bond ◽  
Bond Forming ◽  
Synthetic Strategy ◽  
Carbon Carbon Bond ◽  
Wide Range ◽  
Simple Protocol

Asymmetric hydrocarbofunctionalizations of alkenes has emerged as an efficient synthetic strategy for accessing optically active molecules via carbon-carbon bond-forming process from readily available alkenes and carbo-electrophiles. Herein, we present a summary of the efforts from our group to control the regio- and enantioselectivity of hydrocarbofunctionalizations of electron-deficient alkenes with a nickel catalyst and chiral bisoxazolidine ligand. The reaction undergoes electron-reversed hydrocarbofunctionalizations acrylamides with excellent enantioselectivity. This operationally simple protocol enables the asymmetric hydroalkylation, hydrobenzylation and hydropropargylation of acrylamides. This reaction is useful for preparing a wide range of α-branched chiral amides with broad functional group tolerance.

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.

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