ChemInform Abstract: Activation of a C(sp3)-H Bond by a Transient σ-Alkylpalladium(II) Complex: Synthesis of Spirooxindoles Through a Palladium-Catalyzed Domino Carbopalladation/C(sp3)-C(sp3) Bond-Forming Process.

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.

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Palladium-Catalyzed Three-Component Synthesis of 3-(Diarylmethylene)oxindoles through a Domino Sonagashira/Carbopalladation/CH Activation/CC Bond-Forming Sequence

Angewandte Chemie International Edition ◽

10.1002/anie.200605192 ◽

2007 ◽

Vol 46 (18) ◽

pp. 3291-3295 ◽

Cited By ~ 149

Author(s):

Artur Pinto ◽

Luc Neuville ◽

Jieping Zhu

Keyword(s):

Bond Forming ◽

Palladium Catalyzed

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

ChemInform ◽

10.1002/chin.201227035 ◽

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

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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

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.12.289 ◽

2016 ◽

Vol 12 ◽

pp. 2898-2905 ◽

Cited By ~ 2

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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