Reaction of ?-cyanoacrylic acid catalyzed by tertiary amines

1989 ◽  
Vol 38 (11) ◽  
pp. 2429-2431 ◽  
Author(s):  
I. I. Kandror ◽  
I. O. Bragina ◽  
M. A. Galkina ◽  
B. D. Lavrukhin ◽  
Yu. G. Gololobov
Keyword(s):  
Tertiary Amines ◽  
Cyanoacrylic Acid ◽  
Acid Catalyzed

ChemInform Abstract: Reaction of α-Cyanoacrylic Acid Catalyzed by Tertiary Amines.

ChemInform ◽  
1990 ◽  
Vol 21 (26) ◽  
Author(s):  
I. I. KANDROR ◽  
I. O. BRAGINA ◽  
M. A. GALKINA ◽  
B. D. LAVRUKHIN ◽  
YU. G. GOLOLOBOV
Keyword(s):  
Tertiary Amines ◽  
Cyanoacrylic Acid ◽  
Acid Catalyzed

Synthesis of tertiary amines by direct Brønsted acid catalyzed reductive amination

2020 ◽  
Vol 56 (61) ◽  
pp. 8691-8694
Author(s):  
Mohanad A. Hussein ◽  
An H. Dinh ◽  
Vien T. Huynh ◽  
Thanh Vinh Nguyen
Keyword(s):  
Carbonyl Compounds ◽  
Reductive Amination ◽  
Bronsted Acid ◽  
Tertiary Amines ◽  
Brønsted Acid ◽  
Triflic Acid ◽  
Brönsted Acid ◽  
Acid Catalyzed

Triflic acid efficiently promotes the reductive amination reactions of carbonyl compounds on a broad range of substrates.

Salts of ?-cyanoacrylic acid with sterically hindered tertiary amines

1992 ◽  
Vol 41 (1) ◽  
pp. 176-178 ◽  
Author(s):  
I. I. Kandror ◽  
B. D. Lavrukhin ◽  
M. A. Galkina ◽  
Yu. G. Gololobov
Keyword(s):  
Tertiary Amines ◽  
Cyanoacrylic Acid ◽  
Sterically Hindered

Organocatalyzed [3+3] Annulations for the Construction of Heterocycles

Synthesis ◽  
2020 ◽  
Vol 52 (08) ◽  
pp. 1181-1202
Author(s):  
Yannan Zhu ◽  
You Huang
Keyword(s):  
Nitrogen Heterocycles ◽  
Heterocyclic Carbenes ◽  
Secondary Amines ◽  
Tertiary Amines ◽  
Lewis Bases ◽  
Hydrogen Bonding Interactions ◽  
Chiral Phosphoric Acid ◽  
Oxygen Heterocycles ◽  
Sulfur Heterocycles ◽  
Acid Catalyzed

Six-membered heterocyclic systems are widely distributed in many natural products and pharmaceuticals, and the construction of highly functionalized six-membered heterocyclic compounds is an important topic in modern organic synthesis. Organocatalyzed [3+3] annulations represents an important method for assembling a substantial variety of six-membered cycles that contain one or more heteroatoms. This review describes the development of organocatalyzed [3+3] annulations for the synthesis of six-membered heterocycles, including organocatalysis using secondary amines, tertiary amines, phosphines, chiral phosphoric acids and N-heterocyclic carbenes.1 Introduction2 Secondary Amine Catalyzed [3+3] Annulations2.1 Synthesis of Nitrogen Heterocycles2.2 Synthesis of Oxygen Heterocycles2.3 Synthesis of Sulfur Heterocycles3 Tertiary Amine Catalyzed [3+3] Annulations3.1 Catalysis through Multiple Hydrogen-Bonding Interactions3.2 Catalysis of Tertiary Amines as Lewis Bases4 Phosphine-Catalyzed [3+3] Annulations4.1 Synthesis of Nitrogen Heterocycles4.2 Synthesis of Oxygen Heterocycles4.3 Synthesis of Heterocycles Containing Two or More Heteroatoms5 Chiral Phosphoric Acid Catalyzed [3+3] Annulations5.1 Synthesis of Nitrogen Heterocycles5.2 Synthesis of Heterocycles Containing Two or More Heteroatoms6 N-Heterocyclic Carbene Catalyzed [3+3] Annulations6.1 Synthesis of Nitrogen Heterocycles6.2 Synthesis of Oxygen Heterocycles6.3 Synthesis of Heterocycles Containing Two or More Heteroatoms7 Conclusion and Outlook

Acid Catalyzed Furan Ring Transposition

10.1039/sp768 ◽  
2014 ◽  
Author(s):  
Jamsheena V. ◽  
Ravindra Phatake
Keyword(s):  
Furan Ring ◽  
Acid Catalyzed

Catalytic Carbonyl-Olefin Metathesis of Aliphatic Ketones: Iron(III) HomoDimers as Lewis Acidic Superelectrophiles

2018 ◽  
Author(s):  
Haley Albright ◽  
Paul S. Riehl ◽  
Christopher C. McAtee ◽  
Jolene P. Reid ◽  
Jacob R. Ludwig ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Olefin Metathesis ◽  
Acid Activation ◽  
Lewis Acid Catalysts ◽  
Distinct Mode ◽  
Aliphatic Ketones ◽  
Carbon Carbon Bond ◽  
Metathesis Reactions ◽  
Acid Catalyzed

<div>Catalytic carbonyl-olefin metathesis reactions have recently been developed as a powerful tool for carbon-carbon bond</div><div>formation. However, currently available synthetic protocols rely exclusively on aryl ketone substrates while the corresponding aliphatic analogs remain elusive. We herein report the development of Lewis acid-catalyzed carbonyl-olefin ring-closing metathesis reactions for aliphatic ketones. Mechanistic investigations are consistent with a distinct mode of activation relying on the in situ formation of a homobimetallic singly-bridged iron(III)-dimer as the active catalytic species. These “superelectrophiles” function as more powerful Lewis acid catalysts that form upon association of individual iron(III)-monomers. While this mode of Lewis acid activation has previously been postulated to exist, it has not yet been applied in a catalytic setting. The insights presented are expected to enable further advancement in Lewis acid catalysis by building upon the activation principle of “superelectrophiles” and broaden the current scope of catalytic carbonyl-olefin metathesis reactions.</div>

Mechanistic Insights into Fe Catalyzed α-C-H Oxidations of Tertiary Amines

2019 ◽  
Author(s):  
Christopher J. Legacy ◽  
Frederick T. Greenaway ◽  
Marion Emmert
Keyword(s):  
Free Radical ◽  
Catalytic Mechanism ◽  
Catalyst System ◽  
Oxidation Products ◽  
Tertiary Amines ◽  
Catalyst Activation ◽  
Rate Determining Step ◽  
Fe Catalyst ◽  
Ligand Coordination ◽  
Rate Kinetics

We report detailed mechanistic investigations of an iron-based catalyst system, which allows the α-C-H oxidation of a wide variety of amines, including acyclic tertiary aliphatic amines, to afford dealkylated or amide products. In contrast to other catalysts that affect α-C-H oxidations of tertiary amines, the system under investigation employs exclusively peroxy esters as oxidants. More common oxidants (e.g. tBuOOH) previously reported to affect amine oxidations via free radical pathways do not provide amine α-C-H oxidation products in combination with the herein described catalyst system. Motivated by this difference in reactivity to more common free radical systems, the investigations described herein employ initial rate kinetics, kinetic profiling, Eyring studies, kinetic isotope effect studies, Hammett studies, ligand coordination studies, and EPR studies to shed light on the Fe catalyst system. The obtained data suggest that the catalytic mechanism proceeds through C-H abstraction at a coordinated substrate molecule. This rate-determining step occurs either at an Fe(IV) oxo pathway or a 2-electron pathway at a Fe(II) intermediate with bound oxidant. We further show via kinetic profiling and EPR studies that catalyst activation follows a radical pathway, which is initiated by hydrolysis of PhCO3 tBu to tBuOOH in the reaction mixture. Overall, the obtained mechanistic data support a non-classical, Fe catalyzed pathway that requires substrate binding, thus inducing selectivity for α-C-H functionalization.<br>

Arylboronic Acid-Catalyzed C-Allylation of Unprotected Oximes

2019 ◽  
Author(s):  
Juha Siitonen ◽  
Padmanabha V. Kattamuri ◽  
Muhammed Yousufuddin ◽  
Laszlo Kurti
Keyword(s):  
Total Synthesis ◽  
Acid Catalysts ◽  
Mechanistic Studies ◽  
Arylboronic Acid ◽  
Synthetic Utility ◽  
Acid Catalyzed

Unprotected keto- and aldoximes are readily <i>C</i>-allylated with allyl diisopropyl boronate in the presence of arylboronic acid catalysts to yield highly-substituted <i>N</i>-alpha-secondary (2°) and tertiary (3°) hydroxylamines. The method’s synthetic utility is demonstrated with the total synthesis of the trace alkaloid <i>N</i>-methyl-euphococcine. Preliminary experimental and computational mechanistic studies point toward the formation of a boroxine as the active allylating species.<br>

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