Related Experiment Video
Updated: Nov 20, 2025

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
Tris(pentafluorophenyl)borane catalyzed C-C and C-heteroatom bond formation
Gautam Kumar1, Sourav Roy1, Indranil Chatterjee1
1Department of Chemistry, Indian Institute of Technology Ropar, Nangal Road, Rupnagar, Punjab-140001, India. indranil.chatterjee@iitrpr.ac.in.
Tris(pentafluorophenyl)borane (BCF) is a versatile Lewis acid catalyst driving metal-free organic synthesis. This review highlights recent BCF-catalyzed transformations for C-C and C-heteroatom bond formation since 2018.
Area of Science:
- Organic Chemistry
- Catalysis
- Materials Science
Background:
- Boron-based Lewis acids are crucial in catalysis.
- Tris(pentafluorophenyl)borane (BCF) is a prominent Lewis acid due to its stability and availability.
- BCF catalysis has seen significant exploration in the last two decades.
Purpose of the Study:
- To review recent advancements in BCF-mediated metal-free catalysis.
- To consolidate knowledge on BCF's role in organic transformations.
- To focus on literature published from 2018 onwards.
Main Methods:
- Literature review of BCF catalysis.
- Categorization of reactions based on bond formation (C-C and C-heteroatom).
- Analysis of BCF's catalytic activity in various organic reactions.
Main Results:
- BCF is effective in promoting diverse metal-free catalytic reactions.
- Significant progress in C-C and C-heteroatom bond formation using BCF.
- Emerging catalytic reactivities of BCF are under continuous investigation.
Conclusions:
- BCF is a powerful tool for sustainable, metal-free synthesis.
- The scope of BCF catalysis continues to expand.
- Recent studies underscore BCF's importance in modern organic chemistry.
More Related Videos
Related Concept Videos
Hydroboration-Oxidation of Alkenes
Hybridization of Atomic Orbitals I
Hybridization of Atomic Orbitals II
Halogenation of Alkenes
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.

