scholarly journals Eco-efficient electrocatalytic C–P bond formation

2017 ◽  
Vol 89 (3) ◽  
pp. 311-330 ◽  
Author(s):  
Yulia H. Budnikova ◽  
Tatyana V. Gryaznova ◽  
Valeriya V. Grinenko ◽  
Yulia B. Dudkina ◽  
Mikhail N. Khrizanforov
Keyword(s):  
Organic Chemistry ◽  
Recent Progress ◽  
Bond Formation ◽  
White Phosphorus ◽  
Organic Media ◽  
Phosphine Oxides ◽  
Catalytic Systems ◽  
Oxidative Processes ◽  
Metal Catalyzed ◽  
Perfluoroalkyl Halides

AbstractThe development of practical, efficient and atom-economical methods of formation of carbon-phosphorus bonds remains a topic of considerable interest for the current synthetic organic chemistry and electrochemistry. This review summarizes selected topics from the recent publications with particular emphasis on phosphine and phosphine oxides formation from white phosphorus, chlorophosphines in electrocatalytic processes using aryl, hetaryl or perfluoroalkyl halides as reagents. This review includes selected highlights concerning recent progress in modification of catalytic systems for aromatic C–H bonds phosphonation involving metal-catalyzed ligand directed or metal-induced oxidative processes. Furthermore, a part of this review is devoted to phosphorylation of olefins with white phosphorus under reductive conditions in water-organic media. Finally, we have also documented recent advances in ferrocene C–H activation and phosphorylation.

Recent Advances in Metal-Catalyzed Heterocyclic C-P Bond Formation

2020 ◽  
Vol 17 ◽  
Author(s):  
Feng Xu ◽  
Yu Hui
Keyword(s):  
Organic Synthesis ◽  
Recent Progress ◽  
Bond Activation ◽  
Low Cost ◽  
Bond Formation ◽  
Phosphorus Compounds ◽  
Catalytic Systems ◽  
Phosphorus Containing ◽  
Synthetic Pesticides ◽  
Metal Catalyzed

Abstract:: The Phosphorus-containing heterocycles are an important class of compounds in organic chemistry. Because of their potential application in many fields, especially the synthetic pesticides, medicine and catalyst, the Phosphorus-containing heterocycles have attracted continuous attention by organic synthesis scientists. The development of efficient and low-cost catalytic systems is great interest for construction heterocycles C–P bond. Usually, the Phosphorus-containing heterocycles is prepared via direct carbon–hydrogen (C–H) bond activation or pre-functionalized of heterocycles with carbon–hydrogen （ P-H） bond of phosphorus compounds reaction by metal-catalyzed. This review summarizes recent progress in the heterocycles C-P bond formation reactions by metal-catalyzed, which mainly focusing on the discussion of the reaction mechanism. Aims to provide efficient methods for the future synthesis and application in this field.

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.

Air-stable phosphine oxides as preligands for catalytic activation reactions of C-Cl, C-F, and C-H bonds

2006 ◽  
Vol 78 (2) ◽  
pp. 209-214 ◽  
Author(s):  
Lutz Ackermann ◽  
Robert Born ◽  
Julia H. Spatz ◽  
Andreas Althammer ◽  
Christian J. Gschrei
Keyword(s):  
Bond Activation ◽  
Bond Formation ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Phosphine Oxides ◽  
Aryl Chlorides ◽  
Catalytic Activation ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed ◽  
Metal Catalyzed

Studies on the use of easily accessible heteroatom-substituted secondary phosphine oxides as preligands for cross-coupling reactions are described. These air-stable sterically hindered phosphine oxides allow for efficient palladium-catalyzed Suzuki- and nickel-catalyzed Kumada-coupling reactions using electronically deactivated aryl chlorides. In addition, they enable nickel-catalyzed coupling reactions of magnesium organyls with aryl fluorides at ambient temperature, and ruthenium-catalyzed coupling reactions of aryl chlorides via C-H bond activation. Finally, the application of modular diamino phosphine chlorides as preligands for a variety of transition-metal-catalyzed C-C and C-N bond formation reactions employing electron-rich aryl chlorides is presented.

A Review on Metal-Free Oxidative α-Cyanation and Alkynylation of N-Substituted Tetrahydroisoquinolines as a Rapid Route for the Synthesis of Isoquinoline Alkaloids

2020 ◽  
Vol 24 (8) ◽  
pp. 809-816
Author(s):  
Vladimir V. Kouznetsov ◽  
Marlyn C. Ortiz-Villamizar ◽  
Leonor Y. Méndez-Vargas ◽  
Carlos E. Puerto Galvis
Keyword(s):  
Organic Chemistry ◽  
Recent Progress ◽  
Critical Discussion ◽  
Research Field ◽  
Isoquinoline Alkaloids ◽  
Significant Progress ◽  
Vast Number ◽  
Metal Free ◽  
Scope Of Application ◽  
Metal Catalyzed

As a fast-growing research field in modern organic chemistry, the crossdehydrogenative coupling (CDC) has seen considerable development in its scope of application, uptake into industry, and understanding of its mechanism to functionalize the tetrahydroisoquinoline (THIQ) scaffold. Among the vast number of possibilities offered by the CDC coupling, the metal-free oxidative α-cyanation and alkynylation reactions have emerged as powerful strategies in the synthesis of diverse and potentially bioactive THIQs. Even though transition-metal catalyzed CDC reactions have undoubtedly made significant progress in THIQ chemistry, general and selective protocols for the metal-free oxidative α-cyanation and alkynylation reactions of THIQs are urgently needed. Thereby, this critical discussion is aimed to highlight the recent progress in this field of CDC reactions where Csp3-H bonds are activated without metal catalysts to introduce the CN and the alkynyl groups into the THIQ core.

Carbon Dioxide-Mediated C(sp2)–H Arylation of Primary and Secondary Benzylamines

2018 ◽  
Author(s):  
Mohit Kapoor ◽  
Pratibha Chand-Thakuri ◽  
Michael Young
Keyword(s):  
Carbon Dioxide ◽  
Transition Metal ◽  
Bond Activation ◽  
Bond Formation ◽  
Carbon Bond ◽  
Chelate Effect ◽  
Free Amine ◽  
Carbon Carbon Bond ◽  
New Strategy ◽  
Metal Catalyzed

Carbon-carbon bond formation by transition metal-catalyzed C–H activation has become an important strategy to fabricate new bonds in a rapid fashion. Despite the pharmacological importance of <i>ortho</i>-arylbenzylamines, however, effective <i>ortho</i>-C–C bond formation from C–H bond activation of free primary and secondary benzylamines using Pd<sup>II</sup> remains an outstanding challenge. Presented herein is a new strategy for constructing <i>ortho</i>-arylated primary and secondary benzylamines mediated by carbon dioxide (CO<sub>2</sub>). The use of CO<sub>2</sub> is critical to allowing this transformation to proceed under milder conditions than previously reported, and that are necessary to furnish free amine products that can be directly used or elaborated without the need for deprotection. In cases where diarylation is possible, a chelate effect is demonstrated to facilitate selective monoarylation.

Modern Organic Synthesis in the Laboratory

2008 ◽  
Author(s):  
Jie Jack Li ◽  
Chris Limberakis ◽  
Derek A. Pflum
Keyword(s):  
Organic Chemistry ◽  
Graduate Students ◽  
Organic Synthesis ◽  
Functional Group ◽  
Bond Formation ◽  
Reaction Conditions ◽  
Carbon Bond ◽  
Oxidation Reduction ◽  
Carbon Carbon Bond ◽  
Daunting Task

Searching for reaction in organic synthesis has been made much easier in the current age of computer databases. However, the dilemma now is which procedure one selects among the ocean of choices. Especially for novices in the laboratory, it becomes a daunting task to decide what reaction conditions to experiment with first in order to have the best chance of success. This collection intends to serve as an "older and wiser lab-mate" one could have by compiling many of the most commonly used experimental procedures in organic synthesis. With chapters that cover such topics as functional group manipulations, oxidation, reduction, and carbon-carbon bond formation, Modern Organic Synthesis in the Laboratory will be useful for both graduate students and professors in organic chemistry and medicinal chemists in the pharmaceutical and agrochemical industries.

Recent Progress in Iodine‐Catalysed C−O/C−N Bond Formation of 1,3‐Oxazoles: A Comprehensive Review

2021 ◽  
Vol 6 (4) ◽  
pp. 754-787
Author(s):  
Sanjeev Dhawan ◽  
Vishal Kumar ◽  
Pankaj S. Girase ◽  
Sithabile Mokoena ◽  
Rajshekhar Karpoormath
Keyword(s):  
Recent Progress ◽  
Bond Formation ◽  
Comprehensive Review

Aryl—Aryl Bond Formation by Transition-Metal-Catalyzed Direct Arylation

ChemInform ◽  
2007 ◽  
Vol 38 (22) ◽  
Author(s):  
Dino Alberico ◽  
Mark E. Scott ◽  
Mark Lautens
Keyword(s):  
Transition Metal ◽  
Bond Formation ◽  
Direct Arylation ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

A review of the recent progress on heterogeneous catalysts for Knoevenagel condensation

2021 ◽  
Vol 50 (13) ◽  
pp. 4445-4469
Author(s):  
Jimmy Nelson Appaturi ◽  
Rajni Ratti ◽  
Bao Lee Phoon ◽  
Samaila Muazu Batagarawa ◽  
Israf Ud Din ◽  
...  
Keyword(s):  
Organic Chemistry ◽  
Green Chemistry ◽  
Heterogeneous Catalysts ◽  
Recent Progress ◽  
Knoevenagel Condensation ◽  
Sustainable Production ◽  
Organic Reactions ◽  
Synthetic Organic Chemistry

One of the most crucial attributes of synthetic organic chemistry is to design organic reactions under the facets of green chemistry for the sustainable production of chemicals.

ChemInform Abstract: New Access to H-Phosphonates via Metal-Catalyzed Phosphorus—Oxygen Bond Formation.

ChemInform ◽  
2008 ◽  
Vol 39 (1) ◽  
Author(s):  
Laetitia Coudray ◽  
Isabelle Abrunhosa-Thomas ◽  
Jean-Luc Montchamp
Keyword(s):  
Bond Formation ◽  
Metal Catalyzed ◽  
Oxygen Bond
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