scholarly journals Synthetic Strategy for Pyrazolo[1,5-a]pyridine and Pyrido[1,2-b]indazole Derivatives through AcOH and O2-Promoted Cross-dehydrogenative Coupling Reactions between 1,3-Dicarbonyl Compounds and N-Amino-2-iminopyridines

ACS Omega ◽  
2019 ◽  
Vol 4 (12) ◽  
pp. 15289-15303 ◽  
Author(s):  
Haider Behbehani ◽  
Hamada Mohamed Ibrahim
Keyword(s):  
Coupling Reactions ◽  
Dicarbonyl Compounds ◽  
Synthetic Strategy ◽  
Dehydrogenative Coupling

scholarly journals Intermolecular dialkylation of alkenes with two distinct C(sp3)─H bonds enabled by synergistic photoredox catalysis and iron catalysis

2019 ◽  
Vol 5 (3) ◽  
pp. eaav9839 ◽  
Author(s):  
Xuan-Hui Ouyang ◽  
Yang Li ◽  
Ren-Jie Song ◽  
Ming Hu ◽  
Shenglian Luo ◽  
...  
Keyword(s):  
Functional Group ◽  
Coupling Reactions ◽  
Photoredox Catalysis ◽  
Dicarbonyl Compounds ◽  
Iron Catalysis ◽  
Reduction Potentials ◽  
Dehydrogenative Coupling ◽  
Promotion System ◽  
Carbon Carbon Bonds ◽  
Single Reaction

The functionalization of unactivated C(sp3)─H bonds represents one of the most powerful and most atom-economical tools for the formation of new carbon-based chemical bonds in synthesis. Although cross-dehydrogenative coupling reactions of two distinct C─H bonds for the formation of carbon-carbon bonds have been well investigated, controlled functionalizations of two or more different C(sp3)─H bonds across a functional group or a molecule (e.g., an alkene or alkyne) in a single reaction remain challenging. Here, we present a three-component dialkylation of alkenes with common alkanes and 1,3-dicarbonyl compounds via synergistic photoredox catalysis and iron catalysis for the synthesis of two functionalized 1,3-dicarbonyl compounds. Mechanistic studies suggest that the photoredox catalysis serves as a promotion system to allow the dialkylation to proceed under mild conditions by reducing the oxidation and reduction potentials of the iron intermediates and the reaction partners.

Transition-Metal-Free Synthetic Strategies for the Cross-Coupling Reactions in Water: A Green Approach

2020 ◽  
Vol 07 ◽  
Author(s):  
Tanmay Chatterjee ◽  
Nilanjana Mukherjee
Keyword(s):  
Transition Metal ◽  
Organic Solvents ◽  
Aqueous Media ◽  
Cross Coupling ◽  
Transition Metal Catalysts ◽  
Synthetic Methods ◽  
Coupling Reactions ◽  
Organic Transformations ◽  
Green Approach ◽  
Dehydrogenative Coupling

Abstract: A natural driving force is always working behind the synthetic organic chemists towards the development of ‘green’ synthetic methodologies for the synthesis of useful classes of organic molecules having potential applications. The majority of the essential classes of organic transformations, including C-C and C-X (X = heteroatom) bond-forming crosscoupling reactions, cross dehydrogenative-coupling (CDC) mostly rely on the requirement of transition-metal catalysts and hazardous organic solvents. Hence, the scope in developing green synthetic strategies by avoiding the use of transitionmetal catalysts and hazardous organic solvents for those important and useful classes of organic transformations is very high. Hence, several attempts are made so far. Water being the most abundant, cheap, and green solvent in the world; numerous synthetic methods have been developed in an aqueous medium. In this review, the development of transitionmetal- free green synthetic strategies for various important classes of organic transformations such as C-C and C-X bondforming cross-coupling, cross dehydrogenative-coupling, and oxidative-coupling in an aqueous media is discussed.

Tunable Ligand Effects on Ruthenium Catalyst Activity for Selectively Preparing Imines or Amides by Dehydrogenative Coupling Reactions of Alcohols and Amines

2017 ◽  
Vol 23 (52) ◽  
pp. 12795-12804 ◽  
Author(s):  
Takafumi Higuchi ◽  
Risa Tagawa ◽  
Atsuhiro Iimuro ◽  
Shoko Akiyama ◽  
Haruki Nagae ◽  
...  
Keyword(s):  
Catalyst Activity ◽  
Ruthenium Catalyst ◽  
Coupling Reactions ◽  
Ligand Effects ◽  
Dehydrogenative Coupling

scholarly journals Versatile synthesis and biological evaluation of novel 3’-fluorinated purine nucleosides

2015 ◽  
Vol 11 ◽  
pp. 2509-2520 ◽  
Author(s):  
Hang Ren ◽  
Haoyun An ◽  
Paul J Hatala ◽  
William C Stevens ◽  
Jingchao Tao ◽  
...  
Keyword(s):  
Tumor Cell ◽  
Biological Evaluation ◽  
Purine Nucleoside ◽  
Coupling Reactions ◽  
Cell Growth Inhibition ◽  
Cross Coupling Reactions ◽  
Synthetic Strategy ◽  
Cancer Tumor ◽  
Purine Ring ◽  
Synthesis And Biological Evaluation

A unified synthetic strategy accessing novel 3'-fluorinated purine nucleoside derivatives and their biological evaluation were achieved. Novel 3’-fluorinated analogues were constructed from a common 3’-deoxy-3’-fluororibofuranose intermediate. Employing Suzuki and Stille cross-coupling reactions, fifteen 3’-fluororibose purine nucleosides 1–15 and eight 3’-fluororibose 2-chloro/2-aminopurine nucleosides 16–23 with various substituents at position 6 of the purine ring were efficiently synthesized. Furthermore, 3’-fluorine analogs of natural products nebularine and 6-methylpurine riboside were constructed via our convergent synthetic strategy. Synthesized nucleosides were tested against HT116 (colon cancer) and 143B (osteosarcoma cancer) tumor cell lines. We have demonstrated 3’-fluorine purine nucleoside analogues display potent tumor cell growth inhibition activity at sub- or low micromolar concentration.

scholarly journals Iminoiodane- and Brønsted Base-Mediated Cross Dehydrogenative Coupling of Cyclic Ethers with 1,3-Dicarbonyl Compounds

Molecules ◽  
2015 ◽  
Vol 20 (7) ◽  
pp. 13336-13353 ◽  
Author(s):  
Ciputra Tejo ◽  
Xiao Sim ◽  
Bo Lee ◽  
Benjamin Ayers ◽  
Chung-Hang Leung ◽  
...  
Keyword(s):  
Cyclic Ethers ◽  
Dicarbonyl Compounds ◽  
Dehydrogenative Coupling ◽  
Brønsted Base

Catalytic enantioselective cross dehydrogenative coupling of sp3 C–H of heterocycles

2019 ◽  
Vol 17 (45) ◽  
pp. 9683-9692 ◽  
Author(s):  
Shikha Gandhi
Keyword(s):  
Coupling Reactions ◽  
Dehydrogenative Coupling ◽  
Recent Developments

The recent developments in the asymmetric functionalization of heterocycles via the catalytic enantioselective cross dehydrogenative coupling reactions of heterocyclic sp3 C–H bonds are highlighted in this review.

Sign in / Sign up

Export Citation Format

Share Document