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Formal Anti-Markovnikov Hydroamination of Terminal Olefins.

ABSTRACT: A new strategy to access linear amines from terminal olefin precursors is reported. This two-step, one-pot hydroamination methodology employs sequential oxidation and reduction catalytic cycles. The formal hydroamination transformation proceeds with excellent regioselectivity, and only the anti-Markovnikov product is observed. Up to 70% yield can be obtained from styrenes or aliphatic olefins and either primary or secondary aromatic amines. Additionally, the scope is broad with respect to the olefin and accommodates a variety of functionalities; we demonstrate that amines with removable aryl protecting groups may be utilized to allow access to a more diverse array of hydroamination adducts.

SUBMITTER: Bronner SM

PROVIDER: S-EPMC3855355 | biostudies-literature | 2014 Jan

REPOSITORIES: biostudies-literature

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Formal Anti-Markovnikov Hydroamination of Terminal Olefins.

Bronner Sarah M SM Grubbs Robert H RH

Chemical science 20140101 1

A new strategy to access linear amines from terminal olefin precursors is reported. This two-step, one-pot hydroamination methodology employs sequential oxidation and reduction catalytic cycles. The formal hydroamination transformation proceeds with excellent regioselectivity, and only the anti-Markovnikov product is observed. Up to 70% yield can be obtained from styrenes or aliphatic olefins and either primary or secondary aromatic amines. Additionally, the scope is broad with respect to the ol ...[more]

PMID: 24327829

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