Indium triflate mediated tandem acetalisation-acetal exchange reactions under solvent-free conditions

Brendan M. Smith; Andrew E. Graham

doi:10.1016/j.tetlet.2011.09.087

Indium triflate mediated tandem acetalisation-acetal exchange reactions under solvent-free conditions

Brendan M. Smith, Andrew E. Graham^*

^*Corresponding author for this work

Faculty of Computing, Engineering and Science

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

10 Citations (Scopus)

Abstract

Acyclic acetals and ketals undergo exchange reactions in the presence of catalytic quantities of indium(III) triflate and diols to generate the corresponding cyclic acetals and ketals in excellent yield. The protocol is rapid, employs mild conditions and can be adapted to employ solvent-free reaction conditions. We have further developed this methodology to encompass a tandem acetalisation-acetal exchange protocol which provides facile access to cyclic ketals from unreactive ketones also under very mild, solvent-free reaction conditions.

Original language	English
Pages (from-to)	6281-6283
Number of pages	3
Journal	Tetrahedron Letters
Volume	52
Issue number	47
DOIs	https://doi.org/10.1016/j.tetlet.2011.09.087
Publication status	Published - 23 Nov 2011

Keywords

Acetal exchange
Cyclic acetals and ketals
Indium triflate
Solvent-free reactions
Tandem reaction protocol

Access to Document

10.1016/j.tetlet.2011.09.087Licence: CC BY-NC-ND

10 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

@article{aaa3cf157cc64217941415cd1e934193,

title = "Indium triflate mediated tandem acetalisation-acetal exchange reactions under solvent-free conditions",

abstract = "Acyclic acetals and ketals undergo exchange reactions in the presence of catalytic quantities of indium(III) triflate and diols to generate the corresponding cyclic acetals and ketals in excellent yield. The protocol is rapid, employs mild conditions and can be adapted to employ solvent-free reaction conditions. We have further developed this methodology to encompass a tandem acetalisation-acetal exchange protocol which provides facile access to cyclic ketals from unreactive ketones also under very mild, solvent-free reaction conditions. ",

keywords = "Acetal exchange, Cyclic acetals and ketals, Indium triflate, Solvent-free reactions, Tandem reaction protocol",

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

year = "2011",

month = nov,

day = "23",

doi = "10.1016/j.tetlet.2011.09.087",

language = "English",

volume = "52",

pages = "6281--6283",

journal = "Tetrahedron Letters",

issn = "1873-3581",

publisher = "Elsevier",

number = "47",

}

TY - JOUR

T1 - Indium triflate mediated tandem acetalisation-acetal exchange reactions under solvent-free conditions

AU - Smith, Brendan M.

AU - Graham, Andrew E.

PY - 2011/11/23

Y1 - 2011/11/23

N2 - Acyclic acetals and ketals undergo exchange reactions in the presence of catalytic quantities of indium(III) triflate and diols to generate the corresponding cyclic acetals and ketals in excellent yield. The protocol is rapid, employs mild conditions and can be adapted to employ solvent-free reaction conditions. We have further developed this methodology to encompass a tandem acetalisation-acetal exchange protocol which provides facile access to cyclic ketals from unreactive ketones also under very mild, solvent-free reaction conditions.

AB - Acyclic acetals and ketals undergo exchange reactions in the presence of catalytic quantities of indium(III) triflate and diols to generate the corresponding cyclic acetals and ketals in excellent yield. The protocol is rapid, employs mild conditions and can be adapted to employ solvent-free reaction conditions. We have further developed this methodology to encompass a tandem acetalisation-acetal exchange protocol which provides facile access to cyclic ketals from unreactive ketones also under very mild, solvent-free reaction conditions.

KW - Acetal exchange

KW - Cyclic acetals and ketals

KW - Indium triflate

KW - Solvent-free reactions

KW - Tandem reaction protocol

U2 - 10.1016/j.tetlet.2011.09.087

DO - 10.1016/j.tetlet.2011.09.087

M3 - Article

AN - SCOPUS:80054851577

SN - 1873-3581

VL - 52

SP - 6281

EP - 6283

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 47

ER -

Indium triflate mediated tandem acetalisation-acetal exchange reactions under solvent-free conditions

Abstract

Keywords

Access to Document

Fingerprint

Research output

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

Cite this