Zinc-catalyzed chemoselective reduction of tertiary and secondary amides to amines.

16:48 EDT 29th March 2015 | BioPortfolio

Summary of "Zinc-catalyzed chemoselective reduction of tertiary and secondary amides to amines."

General and convenient procedures for the catalytic hydrosilylation of secondary and tertiary amides under mild conditions have been developed. In the presence of inexpensive zinc catalysts, tertiary amides are easily reduced by applying monosilanes. Key to success for the reduction of the secondary amides is the use of zinc triflate and disilanes with dual SiH moieties. The presented hydrosilylations proceed with excellent chemoselectivity in the presence of sensitive ester, nitro, azo, nitrile, olefins, and other functional groups, thus making the method attractive for organic synthesis.


Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock (Germany), Fax: (+49) 381-1281-51113.

Journal Details

This article was published in the following journal.

Name: Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Pages: 12186-92


PubMed Articles [11066 Associated PubMed Articles listed on BioPortfolio]

Mild and Selective Et2Zn-Catalyzed Reduction of Tertiary Amides under Hydrosilylation Conditions.

Diethylzinc (Et2Zn) can be used as an efficient and chemoselective catalyst for the reduction of tertiary amides under mild reaction conditions employing cost-effective polymeric silane (PMHS) as the ...

A novel Pd-catalyzed N-dealkylative carbonylation of tertiary amines for the preparation of amides.

A novel and convenient protocol for the formation of amides via palladium-catalyzed N-dealkylative carbonylation of alkyl tertiary amines has been developed. In the presence of PdCl2(PhCN)2, CuO, PhCN...

General and Chemoselective Bisphosphonylation of Secondary and Tertiary Amides.

With Tf2O as the activation reagent, a mild and general method has been developed for the bisphosphonylation of both secondary and tertiary amides. The protocol is highly efficient and chemoselective,...

Metal-Free Reduction of Secondary and Tertiary N-Phenyl Amides by Tris(pentafluorophenyl)boron Catalyzed Hydrosilylation.

Tris(pentafluorophenyl)boron B(C6F5)3 is an effective catalyst for the hydrosilylative reduction of tertiary and N-phenyl secondary amides. It allows for the mild reduction of a variety of these amide...

Chemoselective reduction of α-keto amides using nickel catalysts.

Ni-catalysts are used for the first time to synthesize highly important α-hydroxy amides and β-amino alcohols from α-keto amides by chemoselective and complete reduction using hydrosilanes. Chemose...

Clinical Trials [1777 Associated Clinical Trials listed on BioPortfolio]

The Use of Bacteriophage Phi X174 to Assess the Immune Competence of HIV-Infected Patients In Vivo

The objective of this study is to evaluate the safety and utility of bacteriophage phi X174 immunization as a tool to assess the immune competence of HIV-infected patients at different sta...

A Retrospective Clinical Records Review of Patients Diagnosed With Gastrointestinal Stromal Tumour at Two Tertiary Institutes in Singapore

To review the characteristics and treatment of gastrointestinal tumours at the two tertiary centres in Singapore

Effects of Chocolate on Motor Symptoms of Parkinson's Disease

Chocolate consumption has long been associated with enjoyment and pleasure. Popular claims confer on chocolate the properties of being a stimulant, relaxant, euphoriant and antidepressant....

Secondary Prevention of coRonary Events After Discharge From Hospital (SPREAD)

This is a randomized, open trial comparing post discharge interventions by community health workers (CHW) to standard care in acute coronary syndrome (ACS) patients. This trial will be co...

Testing a Secondary Prevention Intervention for HIV-Positive Black Young Men Who Have Sex With Men

The proposed research study aims to conduct a culturally-based secondary prevention intervention targeted toward HIV-positive Black young men who have sex with men (B-YMSM) to explore (1) ...

Medical and Biotech [MESH] Definitions

Nitrous acid sodium salt. Used in many industrial processes, in meat curing, coloring, and preserving, and as a reagent in ANALYTICAL CHEMISTRY TECHNIQUES. It is used therapeutically as an antidote in cyanide poisoning. The compound is toxic and mutagenic and will react in vivo with secondary or tertiary amines thereby producing highly carcinogenic nitrosamines.

A family of enzymes that catalyze the stereoselective, regioselective, or chemoselective syn-dehydrogenation reactions. They function by a mechanism that is linked directly to reduction of molecular OXYGEN.

The level of protein structure in which combinations of secondary protein structures (alpha helices, beta sheets, loop regions, and motifs) pack together to form folded shapes called domains. Disulfide bridges between cysteines in two different parts of the polypeptide chain along with other interactions between the chains play a role in the formation and stabilization of tertiary structure. Small proteins usually consist of only one domain but larger proteins may contain a number of domains connected by segments of polypeptide chain which lack regular secondary structure.

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.

Amides composed of unsaturated aliphatic FATTY ACIDS linked with AMINES by an amide bond. They are most prominent in ASTERACEAE; PIPERACEAE; and RUTACEAE; and also found in ARISTOLOCHIACEAE; BRASSICACEAE; CONVOLVULACEAE; EUPHORBIACEAE; MENISPERMACEAE; POACEAE; and SOLANACEAE. They are recognized by their pungent taste and for causing numbing and salivation.

Search BioPortfolio: