Related Experiment Video
Updated: Jun 6, 2025
07:50
Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
9.2K
HOME-Chemistry: hydrazone as organo-metallic equivalent
1Department of Chemistry, and FQRNT Center for Green Chemistry and Catalysis, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A0B8, Canada.
Pure and Applied Chemistry. Chimie Pure Et Appliquee
|November 26, 2024
Summary
This study introduces a sustainable synthetic chemistry strategy using abundant alcohols and aldehydes instead of stoichiometric organometallic reagents. This approach minimizes waste and addresses metal sustainability concerns by releasing water and nitrogen gas.
Area of Science:
- Synthetic Organic Chemistry
- Sustainable Chemistry
- Organometallic Chemistry
Background:
- Modern synthetic chemistry relies heavily on stoichiometric organometallic reagents.
- This reliance generates significant metal halide waste and raises concerns about metal sustainability.
- Existing methods often require organic halides as precursors, further contributing to waste.
Purpose of the Study:
- To develop a general and sustainable strategy for synthetic chemistry.
- To replace stoichiometric organometallic reagents with abundant, naturally occurring feedstocks.
- To minimize waste generation and address metal sustainability issues.
Main Methods:
- Inspired by the Wolff-Kishner reduction, a novel strategy was developed.
- Utilized alcohols, aldehydes, and ketones as direct feedstocks.
- Achieved various chemical transformations with the release of water and nitrogen gas.
Main Results:
- Demonstrated a general strategy for diverse chemical reactions.
- Included 1,2-carbonyl/imine addition, conjugate addition, and carboxylation.
- Enabled olefination, cross-coupling arylation/allylation, alkylation, hydroalkylation, and C-heteroatom formations.
Conclusions:
- The developed strategy offers a sustainable alternative to traditional organometallic chemistry.
- Utilizing abundant feedstocks significantly reduces waste and environmental impact.
- This approach broadens the scope of green chemistry in synthetic applications.
Related Concept Videos
01:23Properties of Organometallic Compounds
953
Organometallic compounds are compounds that contain a carbon–metal bond. Carbon belongs to an organyl group like alkyl, aryl, allyl, or benzyl groups. The metal can be from Group I or Group II of the periodic table, a transition metal, or a semimetal.
953
02:51Metal-Ligand Bonds
20.6K
The hemoglobin in the blood, the chlorophyll in green plants, vitamin B-12, and the catalyst used in the manufacture of polyethylene all contain coordination compounds. Ions of the metals, especially the transition metals, are likely to form complexes.
In these complexes, transition metals form coordinate covalent bonds, a kind of Lewis acid-base interaction in which both of the electrons in the bond are contributed by a donor (Lewis base) to an electron acceptor (Lewis acid). The Lewis acid in...
In these complexes, transition metals form coordinate covalent bonds, a kind of Lewis acid-base interaction in which both of the electrons in the bond are contributed by a donor (Lewis base) to an electron acceptor (Lewis acid). The Lewis acid in...
20.6K
02:41Formation of Halohydrin from Alkenes
12.7K
An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.
12.7K
02:35Electrophilic Addition to Alkynes: Hydrohalogenation
9.8K
Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
9.8K
01:19Diazonium Group Substitution: –OH and –H
2.7K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
2.7K
02:54Coordination Compounds and Nomenclature
21.2K
In most main group element compounds, the valence electrons of the isolated atoms combine to form chemical bonds that satisfy the octet rule. For instance, the four valence electrons of carbon overlap with electrons from four hydrogen atoms to form CH4. The one valence electron leaves sodium and adds to the seven valence electrons of chlorine to form the ionic formula unit NaCl (Figure 1a). Transition metals do not normally bond in this fashion. They primarily form coordinate covalent bonds, a...
21.2K