Iridium(I)-Catalyzed C‒C and C‒N Bond Formation Reactions via Borrowing Hydrogen Strategy.

08:00 EDT 15th April 2019 | BioPortfolio

Summary of "Iridium(I)-Catalyzed C‒C and C‒N Bond Formation Reactions via Borrowing Hydrogen Strategy."

Iridium(I) complexes having an imidazol-2-ylidene ligand with benzylic wingtips efficiently catalyzed the β-alkylation of secondary alcohols with primary alcohols and acceptorless dehydrogenative cyclization of 2-aminobenzyl alcohol with ketones through a borrowing hydrogen pathway. The β-alkylated alcohols, including cholesterol derivatives, and substituted quinolines were obtained in good yields by using a minute amount of catalyst with a catalytic amount of NaOH or KOH under air atmosphere liberating water (and H2 in the case of quinoline synthesis) as the sole-byproduct. Notably, this system demonstrated TONs of 940000 (for β-alkylation of secondary alcohols with primary alcohols by using down to 0.0001 mol% = 1 ppm of catalyst) and 9200 (acceptorless dehydrogenative cyclization of 2-aminobenzyl alcohol with ketones).


Journal Details

This article was published in the following journal.

Name: The Journal of organic chemistry
ISSN: 1520-6904


DeepDyve research library

PubMed Articles [14861 Associated PubMed Articles listed on BioPortfolio]

Stereoselective Synthesis of Cyclohexanes via an Iridium Catalyzed (5 + 1) Annulation Strategy.

An iridium catalyzed method for the synthesis of functionalized cyclohexanes from methyl ketones and 1,5-diols is described. This process operates by two sequential hydrogen borrowing reactions, provi...

Iridium-Catalyzed Asymmetric Allylic Substitution Reactions.

In this review, we summarize the origin and advancements of iridium-catalyzed asymmetric allylic substitution reactions during the past two decades. Since the first report in 1997, Ir-catalyzed asymme...

Iron-Catalyzed Borrowing Hydrogen C-Alkylation of Oxindoles Using Alcohols.

A general and efficient iron-catalyzed C-alkylation of oxindoles has been developed. This borrowing hydrogen approach employs a (cyclopentadienone)iron carbonyl complex (2 mol %) and exhibits a broad ...

Oxidative R1-H/R2-H Cross-Coupling with Hydrogen Evolution.

Oxidative R1-H/R2-H cross-coupling with hydrogen evolution serves as one of the most atom-economical methods for constructing new chemical bonds. This re-action strategy avoids substrate prefunctional...

Hydrogen-driven cofactor regeneration for stereoselective whole-cell C=C bond reduction in Cupriavidus necator.

The coupling of recombinantly expressed oxidoreductases to endogenous hydrogenases for cofactor-recycling permits the omission of organic cosubstrates as sacrificial electron donors in whole-cell biot...

Clinical Trials [3474 Associated Clinical Trials listed on BioPortfolio]

Radical Radiotherapy by External Beam Radiation Versus Radical Radiotherapy With Temporary Iridium Implant Plus External Beam Radiation in Carcinoma of the Prostate

The specific objective of this study is to compare the relative efficacy of the combination of a temporary iridium implant plus external beam irradiation versus standard external beam irra...

Validation of Brief Objective Neurobehavioral Detectors (BOND) in Mild TBI

The Veterans Health Administration (VHA) has stated the need for a brief screening instrument that can assist with the triage of the enormous number of returning OEF/OIF veterans with conc...

Combination of Dental Bleaching Techniques, Randomized Clinical Trial

To determine the effectiveness of combining different concentrations of hydrogen peroxide and carbamide used during tooth bleaching.

Therapeutic Effects of Hydrogen on Steroid-refractory/or Steroid-dependent cGVHD

This study suggested that hydrogen has a potential as an effective and safe therapeutic agent on cGVHD.

Clinical Evaluation of Three Dental Adhesive Systems in Class V Restorations

The purpose of this study is to compare the clinical performance of three dental adhesive systems used to bond Class V cavity fillings in adult teeth.

Medical and Biotech [MESH] Definitions

Unstable isotopes of iridium that decay or disintegrate emitting radiation. Ir atoms with atomic weights 182-190, 192, and 194-198 are radioactive iridium isotopes.

Hydrogen-donating proteins that participates in a variety of biochemical reactions including ribonucleotide reduction and reduction of PEROXIREDOXINS. Thioredoxin is oxidized from a dithiol to a disulfide when acting as a reducing cofactor. The disulfide form is then reduced by NADPH in a reaction catalyzed by THIOREDOXIN REDUCTASE.

Peroxidase catalyzed oxidation of lipids using hydrogen peroxide as an electron acceptor.

A class of enzymes that catalyze the formation of a bond between two substrate molecules, coupled with the hydrolysis of a pyrophosphate bond in ATP or a similar energy donor. (Dorland, 28th ed) EC 6.

Widely distributed enzymes that carry out oxidation-reduction reactions in which one atom of the oxygen molecule is incorporated into the organic substrate; the other oxygen atom is reduced and combined with hydrogen ions to form water. They are also known as monooxygenases or hydroxylases. These reactions require two substrates as reductants for each of the two oxygen atoms. There are different classes of monooxygenases depending on the type of hydrogen-providing cosubstrate (COENZYMES) required in the mixed-function oxidation.

Quick Search


DeepDyve research library

Relevant Topic

Lipitor was the best selling drug in 2009, with the 2009 annual sales coming in at over $5m for its company, Pfizer Inc. Lipitor is the brand name for an atorvastatin calcium medication that is prescribed to lower cholesterol and triglycerides in the the...

Searches Linking to this Article