Related Experiment Video
Updated: Feb 13, 2026
![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)
Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Formal Lossen Rearrangement/[3+2] Annulation Cascade Catalyzed by a Modified Cyclopentadienyl RhIII Complex
Takayuki Yamada1, Yu Shibata1, Susumu Kawauchi1
1Department of Chemical Science and Engineering, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, 152-8550, Japan.
Abstract:
It has been established that a cyclopentadienyl RhIII complex with two phenyl groups and a pendant amide moiety catalyzes the formal Lossen rearrangement/[3+2] annulation cascade of N-pivaloyl benzamides and acrylamides with alkynes leading to substituted indoles and pyrroles. Mechanistic studies revealed that this cascade reaction proceeds via not the Lossen rearrangement to form anilides or enamides but C-H bond cleavage, alkyne insertion, and the formal Lossen rearrangement.
More Related Videos
Related Concept Videos
Formal Charges
Intracellular Signaling Cascades
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Rab Cascades
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement
Lewis Structures and Formal Charges

