Related Experiment Video
Updated: Jun 9, 2026

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
Light-Driven Decarboxylative-Dehydrogenative C(sp3)-C(sp3) Cross-Coupling Enables Amine Diversification
Krishnakumar Sachidanandan1, Monish A Ansari1, Savini Senanayake1
1Department of Chemistry & Chemical Biology, Indiana University Indianapolis, Indianapolis, Indiana 46202, United States.
None:
We report a metal-free, light-driven platform that expands amine chemical space using amino acid derivatives and simple alkanes as carbon-based synthons. The transformation demonstrates an underexplored sequential decarboxylative-dehydrogenative process, employing in situ generated aryl radicals to activate a broad range of C(sp3)-H bonds. Representative amino acids, including glycine, alanine, valine, and leucine derivatives undergo efficient decarboxylative coupling with activated and unactivated C(sp3)-H bonds affording structurally diverse amine products. This strategy underscores the untapped potential of simple next-generation bioderived and hydrocarbon building blocks for light-enabled C(sp3)-C(sp3) cross-couplings as a complementary strategy to reductive amination.
More Related Videos
06:46Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
12:07Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Related Concept Videos
Amines to Amides: Acylation of Amines
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide...
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism
Preparation of Amines: Reductive Amination of Aldehydes and Ketones
Preparation of Amides
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
Amides to Amines: LiAlH4 Reduction
Amide reduction requires two equivalents of the reducing agent, acting as a source of hydride ions. As shown in the figure, the reaction is initiated with a nucleophilic attack by the hydride ion at the carbonyl carbon to form a tetrahedral intermediate.
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...