A Mild Hydroaminoalkylation of Conjugated Dienes Using a Unified Cobalt and Photoredox Catalytic System

Metallo-photoredox catalysis has redefined the available bond disconnections in the synthetic arsenal. By harnessing the one-electron chemistry of photoredox catalysis in tandem with low-valent cobalt catalysts, new methods by which functionalities may be stitched together become available. Herein w...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2017-11, Vol.139 (43), p.15504-15508
Main Authors: Thullen, Scott M, Rovis, Tomislav
Format: Article
Language:English
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Summary:Metallo-photoredox catalysis has redefined the available bond disconnections in the synthetic arsenal. By harnessing the one-electron chemistry of photoredox catalysis in tandem with low-valent cobalt catalysts, new methods by which functionalities may be stitched together become available. Herein we describe the coupling of photoredox-generated α-amino radical species with conjugated dienes using a unified cobalt and iridium catalytic system in order to access a variety of useful homoallylic amines from simple commercially available starting materials. We present a series of mechanistic experiments that support the intervention of Co–hydride intermediates that undergo diene insertion to generate Co−π-allyl species.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.7b09252