ArticleiScience2020
Toward Rational Understandings of α-C-H Functionalization: Energetic Studies of Representative Tertiary Amines.
Article in iScience, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed, 25 citations in OpenAlex.
- Effect of Alternating Polarity in Electrochemical Olefin Hydrocarboxylation.Angewandte Chemie (International ed. in English) · 2025Article
- Oxoammonium-Catalyzed Ether Oxidation via Hydride Abstraction: Methodology Development and Mechanistic Investigation Using Paramagnetic Relaxation Enhancement NMR.Journal of the American Chemical Society · 2024Article
- Polarity-Driven Thiyl Radical-Catalyzed Aerobic Debenzylation of Ethers and Amines.The Journal of organic chemistry · 2024Article
- Oxyethylated Fluoresceine-(thia)calix[4]arene Conjugates: Synthesis and Visible-Light Photoredox Catalysis in Water-Organic Media.Molecules (Basel, Switzerland) · 2022Article
- Contrasteric coupling of allenes and tetrahydroisoquinolines by iron-catalysed allenic C(spChemical communications (Cambridge, England) · 2021Article
- Direct and Efficient C(spFrontiers in chemistry · 2020Article
Corrections and comments
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Authors and funding
3 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Functionalization of α-C-H bonds of tertiary amines to build various α-C-X bonds has become a mainstream in synthetic chemistry nowadays. However, due to lack of fundamental knowledge on α-C-H bond strength as an energetic guideline, rational exploration of new synthetic methodologies remains a far-reaching anticipation. Herein, we report a unique hydricity-based approach to establish the first integrated energetic scale covering both the homolytic and heterolytic energies of α-C-H bonds for 45 representative tertiary amines and their radical cations. As showcased from the studies on tetrahydroisoquinolines (THIQs) by virtue of their thermodynamic criteria, the feasibility and mechanisms of THIQ oxidation were deduced, which, indeed, were found to correspond well with experimental observations. This integrated scale provides a good example to relate bond energetics with mechanisms and thermodynamic reactivity of amine α-C-H functionalization and hence, may be referenced for analyzing similar structure-property problems for various substrates.
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