Ligand-promoted cobalt-catalyzed radical hydroamination of alkenes.

Abstract:

:Highly regio- and enantioselective intermolecular hydroamination of alkenes is a challenging process potentially leading to valuable chiral amines. Hydroamination of alkenes via metal-catalyzed hydrogen atom transfer (HAT) with good regioselectivity and functional group tolerance has been reported, however, high enantioselectivity has not been achieved due to the lack of suitable ligands. Here we report a ligand-promoted cobalt-catalyzed Markovnikov-type selective radical hydroamination of alkenes with diazo compounds. This operationally simple protocol uses unsymmetric NNN-tridentate (UNT) ligand, readily available alkenes and hydrosilanes to construct hydrazones with good functional group tolerance. The hydrazones can undergo nitrogen-nitrogen bond cleavage smoothly to deliver valuable amine derivatives. Additionally, asymmetric intermolecular hydroamination of unactivated aliphatic terminal alkenes using chiral N-imidazolinylphenyl 8-aminoquinoline (IPAQ) ligands has also been achieved to afford chiral amine derivatives with good enantioselectivities.

journal_name

Nat Commun

journal_title

Nature communications

authors

Shen X,Chen X,Chen J,Sun Y,Cheng Z,Lu Z

doi

10.1038/s41467-020-14459-x

subject

Has Abstract

pub_date

2020-02-07 00:00:00

pages

783

issue

1

issn

2041-1723

pii

10.1038/s41467-020-14459-x

journal_volume

11

pub_type

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