Related Experiment Video
Updated: May 22, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
Published on: June 20, 2014
Low-oxidation state indium-catalyzed C-C bond formation.
1The University of Tokyo, Department of Chemistry, School of Science and Graduate School of Pharmaceutical Sciences, Hongo, Japan.
This study introduces the first catalytic use of indium(I) for selective carbon-carbon bond formation. Indium(I) catalysts enable novel, efficient, and enantioselective organic synthesis pathways.
Area of Science:
- Organic Chemistry
- Organometallic Chemistry
- Catalysis
Background:
- Indium catalysis is crucial for selective bond formation due to its low toxicity and functional group tolerance.
- While indium(III) is a well-established Lewis acid catalyst, indium(I)'s catalytic potential remains largely unexplored.
- Indium(I) exhibits ambiphilic properties, acting as both a Lewis acid and base, offering unique reactivity.
Purpose of the Study:
- To develop novel catalytic systems utilizing low-oxidation state indium for carbon-carbon bond formation.
- To explore the ambiphilic nature of indium(I) in activating both nucleophiles and electrophiles.
- To establish efficient and selective synthetic methodologies using indium(I) catalysts.
Main Methods:
- Development of indium(I)-based catalytic systems for reactions involving boron-based pronucleophiles and various electrophiles.
- Utilizing indium(I) iodide for α-selective allylations of C(sp(2)) electrophiles.
- Employing chiral ligands with indium(I) compounds for enantioselective transformations.
- Investigating indium(I) triflate and indium(I) chloride in conjunction with chiral co-catalysts for specific bond formations.
Main Results:
- Indium(I) iodide efficiently catalyzed α-selective allylations of ketones and hydrazones.
- Chiral indium(I) catalysts enabled highly enantioselective allylation, crotylation, and α-chloroallylation of hydrazones with excellent diastereoselectivity.
- Indium(I) triflate proved effective for allylations and propargylations of C(sp(3)) electrophiles, including applications in carbohydrate chemistry.
- A silver-based chiral system with indium(I) chloride facilitated enantioselective allylation and allenylation of N,O-aminals.
Conclusions:
- Low-oxidation state indium catalysts are versatile and efficient for various carbon-carbon bond-forming reactions.
- The ambiphilic nature of indium(I) allows for unique activation modes in catalysis.
- These findings open new avenues for enantioselective synthesis using indium(I) in organic chemistry.
More Related Videos
07:30A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
Published on: January 21, 2020
12:27Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Related Concept Videos
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
Properties of Organometallic Compounds
Radical Reactivity: Intramolecular vs Intermolecular
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism