Metal-catalyzed transformations of propargylic alcohols into α,β-unsaturated carbonyl compounds: from the Meyer–Schuster and Rupe rearrangements to redox isomerizations

2010 ◽  
Vol 39 (17) ◽  
pp. 4015 ◽  
Author(s):  
Victorio Cadierno ◽  
Pascale Crochet ◽  
Sergio E. García-Garrido ◽  
José Gimeno
Keyword(s):  
Carbonyl Compounds ◽  
Propargylic Alcohols ◽  
Metal Catalyzed

Propargylic Alcohols as Coupling Partners in Transition‐Metal‐Catalyzed Arene C−H Activation

2020 ◽  
Vol 362 (23) ◽  
pp. 5238-5256
Author(s):  
Gadi Ranjith Kumar ◽  
Manda Rajesh ◽  
Shuimu Lin ◽  
Shouping Liu
Keyword(s):  
Transition Metal ◽  
Propargylic Alcohols ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

scholarly journals Transition Metal-Catalyzed α-Position Carbon–Carbon Bond Formations of Carbonyl Derivatives

Catalysts ◽  
2020 ◽  
Vol 10 (8) ◽  
pp. 861 ◽  
Author(s):  
Ha-Eun Lee ◽  
Dopil Kim ◽  
Ahrom You ◽  
Myung Hwan Park ◽  
Min Kim ◽  
...  
Keyword(s):  
Transition Metal ◽  
Carbonyl Compounds ◽  
Bond Formation ◽  
Chiral Ligand ◽  
Catalytic Systems ◽  
Carbon Bond ◽  
Carbonyl Derivatives ◽  
Carbon Carbon Bond ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

α-Functionalization of carbonyl compounds in organic synthesis has traditionally been accomplished via classical enolate chemistry. As α-functionalized carbonyl moieties are ubiquitous in biologically and pharmaceutically valuable molecules, catalytic α-alkylations have been extensively studied, yielding a plethora of practical and efficient methodologies. Moreover, stereoselective carbon–carbon bond formation at the α-position of achiral carbonyl compounds has been achieved by using various transition metal–chiral ligand complexes. This review describes recent advances—in the last 20 years and especially focusing on the last 10 years—in transition metal-catalyzed α-alkylations of carbonyl compounds, such as aldehydes, ketones, imines, esters, and amides and in efficient carbon–carbon bond formations. Active catalytic species and ligand design are discussed, and mechanistic insights are presented. In addition, recently developed photo-redox catalytic systems for α-alkylations are described as a versatile synthetic tool for the synthesis of chiral carbonyl-bearing molecules.

Recent Advances in Photocatalytic C–N Bond Coupling Reactions

Synthesis ◽  
2020 ◽  
Author(s):  
Wing-Yiu Yu ◽  
Chun-Ming Chan ◽  
Yip-Chi Chow
Keyword(s):  
Carbonyl Compounds ◽  
Bond Formation ◽  
Coupling Reactions ◽  
Amino Groups ◽  
Cyclization Reactions ◽  
Radical Coupling ◽  
Synthetic Intermediates ◽  
Photocatalytic Reactions ◽  
Metal Catalyzed ◽  
Pharmaceutical Agents

Catalytic C–N bond formation is one of the major research topics in synthetic chemistry owing to the ubiquity of amino groups in natural products, synthetic intermediates and pharmaceutical agents. In parallel with well-established metal-catalyzed C–N bond coupling protocols, photocatalytic reactions have recently emerged as efficient and selective alternatives for the construction of C–N bonds. In this review, the progress made on photocatalytic C–N bond coupling reactions between 2012 and February 2020 is summarized.1 Introduction1.1 General Mechanisms for Photoredox Catalysis1.2 Pioneering Work2 C(sp2)–N Bond Formation2.1 Protocols Involving an External Oxidant2.2 Oxidant-Free Protocols3 C(sp3)–N Bond Formation3.1 Direct Radical–Radical Coupling3.2 Addition Reactions to Alkenes3.3 Reductive Amination of Carbonyl Compounds3.4 Decarboxylative Amination4 Cyclization Reactions4.1 C(sp2)–N Heterocycle Formation4.2 C(sp3)–N Heterocycle Formation5 Other Examples6 Conclusion and Outlook

Thioureas: new ligands for the metal catalyzed asymmetric reduction of carbonyl compounds

1997 ◽  
Vol 8 (19) ◽  
pp. 3319-3326 ◽  
Author(s):  
François Touchard ◽  
Fabienne Fache ◽  
Marc Lemaire
Keyword(s):  
Carbonyl Compounds ◽  
Asymmetric Reduction ◽  
Metal Catalyzed
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