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. 2017 Nov 1;139(43):15504-15508.
doi: 10.1021/jacs.7b09252. Epub 2017 Oct 19.

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

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

Scott M Thullen et al. J Am Chem Soc. .

Abstract

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.

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