Related Experiment Video
Updated: Jan 8, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Copper-Catalyzed 1,2-Diazidation and 1,2-Azidooxygenation of 1,3-Dienes: Three Divergent Protocols Using Zhdankin's
Adriana E Barni1, Megan A George1, Jacob R Pangborn1
1Department of Chemistry and Biochemistry, University of Tampa, Tampa, Florida 33606, United States.
Abstract:
A series of three divergent protocols for the copper-catalyzed azidation of 1,3-dienes using iodine(III) Zhdankin's reagent is reported. This strategy features protocols for 1,2-diazidation, two-component 1,2-azidooxygenation, and three-component 1,2-azidooxygenation of 1,3-dienes in highly chemo-, regio-, and site-selective fashion under mild conditions. Excellent to fair yields are reported for a variety of activated and unactivated 1,3-diene systems with a range of substitution patterns. Additionally, mechanistic investigations are included to provide insights into the underpinnings for the divergence of these protocols and the component requirements.
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
09:35Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Related Concept Videos
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Acid Halides to Ketones: Gilman Reagent
As shown below, the mechanism proceeds in two steps. First, one of the alkyl groups of the reagent acts as a nucleophile and attacks the acyl carbon of the acid chloride to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen...
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction