Scandium as a pre-catalyst for the deoxygenative allylation of benzylic alcohols

Ivan Šolić; Pattarakiat Seankongsuk; Joanna Kejun Loh; Tirayut Vilaivan; Roderick W. Bates

doi:10.1039/c7ob02219k

Scandium as a pre-catalyst for the deoxygenative allylation of benzylic alcohols

Ivan Šolić, Pattarakiat Seankongsuk, Joanna Kejun Loh, Tirayut Vilaivan, Roderick W. Bates^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

28 Citations (Scopus)

Abstract

Scandium triflate is an effective pre-catalyst for the deoxygenative allylation of benzylic alcohols with a narrow substrate window. The reaction is shown to proceed through a "hidden Brønsted acid" mechanism. The reaction is efficient provided that the aryl group is neither too electron rich nor too electron poor. It is shown that this allows useful selectivity. The reaction also works for benzyhydryl alcohols with broader scope. The reaction may also be catalysed by Nafion.

Original language	English
Pages (from-to)	119-123
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	16
Issue number	1
DOIs	https://doi.org/10.1039/c7ob02219k
Publication status	Published - 2017
Externally published	Yes

Bibliographical note

Publisher Copyright:
©2017 Royal Society of Chemistry.

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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AU - Šolić, Ivan

AU - Seankongsuk, Pattarakiat

AU - Loh, Joanna Kejun

AU - Vilaivan, Tirayut

AU - Bates, Roderick W.

PY - 2017

Y1 - 2017

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AB - Scandium triflate is an effective pre-catalyst for the deoxygenative allylation of benzylic alcohols with a narrow substrate window. The reaction is shown to proceed through a "hidden Brønsted acid" mechanism. The reaction is efficient provided that the aryl group is neither too electron rich nor too electron poor. It is shown that this allows useful selectivity. The reaction also works for benzyhydryl alcohols with broader scope. The reaction may also be catalysed by Nafion.

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JF - Organic and Biomolecular Chemistry

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ER -

Scandium as a pre-catalyst for the deoxygenative allylation of benzylic alcohols

Abstract

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