Regioselective Hydroamination Using a Directed Nucleopalladation/Protodepalladation Strategy

John A. Gurak Jr; Keary M. Engle

doi:10.1055/s-0036-1589077

Synlett, Inhaltsverzeichnis

Synlett 2017; 28(16): 2057-2065
DOI: 10.1055/s-0036-1589077

synpacts

Regioselective Hydroamination Using a Directed Nucleopalladation/Protodepalladation Strategy

Autor*innen

John A. Gurak Jr

Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA eMail: keary@scripps.edu
Keary M. Engle *

Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA eMail: keary@scripps.edu

Abstract

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Abstract

Alkene hydroamination is an attractive approach for converting alkenes into structurally complex amine products. Several different strategies have been pursued over the past few decades to achieve this historically challenging reaction. One of the key issues associated with this transformation is control of regioselectivity, which is particularly difficult for internal non-conjugated alkenes. Our group has recently found success using a removable bidentate auxiliary to control regioselectivity and stabilize the key nucleopalladated intermediate in a palladium(II)-catalyzed alkene hydroamination with N–H nucleophiles. This article describes the historical context for this work, the underlying conceptual logic, our results to date, and the future outlook.

Key words

palladium - hydroamination - hydrofunctionalization - nucleopalladation - aza-heterocycles - directing groups

Volltext

Referenzen

References and Notes

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