Related Experiment Video
Updated: Jan 8, 2026

Hydrolysis of a Ni-Schiff-Base Complex Using Conditions Suitable for Retention of Acid-labile Protecting Groups
Published on: April 6, 2017
Deprotective Functionalization: An Emerging Concept for Amine Reactivity
Irmgard Tiefenbrunner1, Saad Shaaban1, Nuno Maulide1
1Faculty of Chemistry, Institute of Organic Chemistry, University of Vienna, Vienna, Austria.
None:
Protecting groups are widely employed in multi-step syntheses with the goal to downregulate the reactivity of certain functional groups. Their use, while often unavoidable, comes with notable drawbacks including increased costs and waste, as well as typically adding two (nonstrategic) synthetic steps to a given sequence. Moreover, late-stage deprotection of highly functionalized compounds can pose challenges. We introduced an approach termed deprotective functionalization, allowing for direct conversion of a protected functional group into a new one without requiring a separate deprotection event. Interestingly, in this paradigm the protecting group not only prevents side reactions, but also primes the protected functionality for selective transformations. This article provides a conceptual framework for this approach and discusses related strategies, currently limited to protected amines.
Related Concept Videos
Amines to Amides: Acylation of Amines
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
Preparation of Amines: Reductive Amination of Aldehydes and Ketones
Acid Halides to Amides: Aminolysis
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
Protection of Alcohols
Protection
It defines a protecting group as the masking agent to make the more reactive species inert to a given set of conditions. This concept is depicted via the illustration of liquid flow through different outlets in an assembly of pipes. The analogy helps to understand the role...
Protecting Groups for Aldehydes and Ketones: Introduction
Preparation of Amines: Alkylation of Ammonia and Amines
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...

