Indium(III) triflate catalysed transacetalisation reactions of diols and triols under solvent-free conditions

Brendan M. Smith; Tomasz M. Kubczyk; Andrew E. Graham

doi:10.1016/j.tet.2012.07.048

Indium(III) triflate catalysed transacetalisation reactions of diols and triols under solvent-free conditions

Brendan M. Smith, Tomasz M. Kubczyk, Andrew E. Graham^*

^*Corresponding author for this work

Faculty of Computing, Engineering and Science

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

11 Citations (Scopus)

Abstract

Acyclic acetals and ketals undergo transacetalisation in the presence of catalytic quantities of indium(III) triflate (In(OTf) ₃) and diols or triols under solvent-free conditions to generate the corresponding cyclic acetals and ketals in excellent yield. The methodology has been further developed to encompass a tandem acetalisation-acetal exchange protocol, which provides a facile and high yielding route to cyclic ketals from unreactive ketones under very mild reaction conditions.

Original language	English
Pages (from-to)	7775-7781
Number of pages	7
Journal	Tetrahedron Letters
Volume	68
Issue number	38
DOIs	https://doi.org/10.1016/j.tet.2012.07.048
Publication status	Published - 23 Sept 2012

Keywords

Glycerol valorisation
Indium(III) triflate
Solvent-free reactions
Tandem reaction protocol
Transacetalisation

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10.1016/j.tet.2012.07.048Licence: CC BY-NC-ND

11 Citations
1 Doctoral Thesis

The Utilisation of Indium(III) Salts as Highly Efficient Catalysts in Organic Synthesis
Smith, B., 2008
Research output: Types of Thesis › Doctoral Thesis

Cite this

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title = "Indium(III) triflate catalysed transacetalisation reactions of diols and triols under solvent-free conditions",

abstract = "Acyclic acetals and ketals undergo transacetalisation in the presence of catalytic quantities of indium(III) triflate (In(OTf) 3) and diols or triols under solvent-free conditions to generate the corresponding cyclic acetals and ketals in excellent yield. The methodology has been further developed to encompass a tandem acetalisation-acetal exchange protocol, which provides a facile and high yielding route to cyclic ketals from unreactive ketones under very mild reaction conditions. ",

keywords = "Glycerol valorisation, Indium(III) triflate, Solvent-free reactions, Tandem reaction protocol, Transacetalisation",

author = "Smith, {Brendan M.} and Kubczyk, {Tomasz M.} and Graham, {Andrew E.}",

year = "2012",

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AU - Smith, Brendan M.

AU - Kubczyk, Tomasz M.

AU - Graham, Andrew E.

PY - 2012/9/23

Y1 - 2012/9/23

N2 - Acyclic acetals and ketals undergo transacetalisation in the presence of catalytic quantities of indium(III) triflate (In(OTf) 3) and diols or triols under solvent-free conditions to generate the corresponding cyclic acetals and ketals in excellent yield. The methodology has been further developed to encompass a tandem acetalisation-acetal exchange protocol, which provides a facile and high yielding route to cyclic ketals from unreactive ketones under very mild reaction conditions.

AB - Acyclic acetals and ketals undergo transacetalisation in the presence of catalytic quantities of indium(III) triflate (In(OTf) 3) and diols or triols under solvent-free conditions to generate the corresponding cyclic acetals and ketals in excellent yield. The methodology has been further developed to encompass a tandem acetalisation-acetal exchange protocol, which provides a facile and high yielding route to cyclic ketals from unreactive ketones under very mild reaction conditions.

KW - Glycerol valorisation

KW - Indium(III) triflate

KW - Solvent-free reactions

KW - Tandem reaction protocol

KW - Transacetalisation

U2 - 10.1016/j.tet.2012.07.048

DO - 10.1016/j.tet.2012.07.048

M3 - Article

AN - SCOPUS:84864584384

SN - 0040-4039

VL - 68

SP - 7775

EP - 7781

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 38

ER -

Indium(III) triflate catalysed transacetalisation reactions of diols and triols under solvent-free conditions

Abstract

Keywords

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Research output

The Utilisation of Indium(III) Salts as Highly Efficient Catalysts in Organic Synthesis

Cite this