Related Experiment Video
Updated: Jun 6, 2025

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Geminal Aminocyanation Enabled by Ylide Mediated Rearrangement
Zichun Yan1, Meirong Huang2, Chuang Wang1
1Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University, Changzhou 213164, China.
Abstract:
Herein, we describe experimental and computational studies to understand the features of oxycyanopyridinium ylides generated in situ from oxy-cyanopyridines and rhodium carbene. This chemistry has enabled the concomitant formation of both C-N and C-C bonds, providing a complementary approach for cyanation reactions. Density functional theory calculations indicate the sequential metal-bound ylide formation, rhodium-associated five-membered transition state, and 1,4-cyano group relocation. Moreover, the enantioselective rearrangement has been realized by using chiral dirhodium complexes as the catalysts.
More Related Videos
Related Concept Videos
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
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...
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Preparation of 1° Amines: Gabriel Synthesis
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Nucleophilic Aromatic Substitution: Elimination–Addition

