Chemistry - A European Journal 2018-04-10

Formal Lossen Rearrangement/[3+2] Annulation Cascade Catalyzed by a Modified Cyclopentadienyl RhIII Complex

Takayuki Yamada; Yu Shibata; Susumu Kawauchi; Soichi Yoshizaki; Ken Tanaka

Index: 10.1002/chem.201801125

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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.