Scandium-catalysed intermolecular hydroaminoalkylation of olefins with aliphatic tertiary amines

Adi E. Nako; Juzo Oyamada; Masayoshi Nishiura; Zhaomin Hou

doi:10.1039/C6SC02129H

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Scandium-catalysed intermolecular hydroaminoalkylation of olefins with aliphatic tertiary amines†

Adi E. Nako,

^a Juzo Oyamada,

^a Masayoshi Nishiura

^a and Zhaomin Hou

*^a

Author affiliations

* Corresponding authors

^a Organometallic Chemistry Laboratory and RIKEN Center for Sustainable Resource Science, RIKEN, 2-1 Hirosawa, Wako, Saitama, Japan
E-mail: houz@riken.jp

Abstract

A homoleptic scandium trialkyl complex in combination with a borate compound served as an excellent catalyst for the C–H addition of aliphatic tertiary amines to olefins. This highly regiospecific, 100% atom efficient C–H bond alkylation reaction was applicable to a wide variety of tertiary amines and olefins, including functionalised styrenes and unactivated α-olefins. This work represents the first example of rare-earth catalysed olefin hydroaminoalkylation and also the first example of catalytic C–H addition of aliphatic tertiary amines to olefins with any catalyst.

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Article information

DOI: https://doi.org/10.1039/C6SC02129H
Article type: Edge Article
Submitted: 14 May 2016
Accepted: 03 Jul 2016
First published: 04 Jul 2016
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry

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Chem. Sci., 2016,7, 6429-6434

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Scandium-catalysed intermolecular hydroaminoalkylation of olefins with aliphatic tertiary amines

A. E. Nako, J. Oyamada, M. Nishiura and Z. Hou, Chem. Sci., 2016, 7, 6429 DOI: 10.1039/C6SC02129H

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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Chemical Science

Scandium-catalysed intermolecular hydroaminoalkylation of olefins with aliphatic tertiary amines†

Abstract

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Scandium-catalysed intermolecular hydroaminoalkylation of olefins with aliphatic tertiary amines

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