Visible-Light Photolysis of Allyl Zirconocenes: A Photoinduced Three-Component Radical (4+2)-Cyclization–Allylation Reaction

Abstract A photoinduced, three-component radical (4+2)-cyclization–allylation reaction between 3-(2-iodoethyl)indoles, acceptor-substituted alkenes, and allyl zirconocenes of the structure Cp 2 ZrCl(σ-allyl) was developed. The protocol leads to highly functionalized hexahydrocarbazoles in a single s...

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Bibliographic Details
Published in:Synlett 2017-05, Vol.28 (8), p.919-923
Main Authors: Alpers, Dirk, Hoffmann, Frank, Brasholz, Malte
Format: Article
Language:English
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Summary:Abstract A photoinduced, three-component radical (4+2)-cyclization–allylation reaction between 3-(2-iodoethyl)indoles, acceptor-substituted alkenes, and allyl zirconocenes of the structure Cp 2 ZrCl(σ-allyl) was developed. The protocol leads to highly functionalized hexahydrocarbazoles in a single step, establishing three C–C bonds and three contiguous stereocenters at once. The radical reaction is initiated by direct photolysis of allyl zirconocenes to generate free allyl radicals.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0036-1588957