An efficient method for the chemoselective synthesis of acylals from aromatic aldehydes using bismuth triflate

Marc D. Carrigan; Kyle J. Eash; Matthew C. Oswald; Ram S. Mohan

doi:10.1016/S0040-4039(01)01756-7

An efficient method for the chemoselective synthesis of acylals from aromatic aldehydes using bismuth triflate

Marc D. Carrigan, Kyle J. Eash, Matthew C. Oswald, Ram S. Mohan

Physical Medicine and Rehabilitation

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

117 Scopus citations

Abstract

Aromatic aldehydes are smoothly converted into the corresponding acylals in good yields in the presence of 0.10 mol% Bi(OTf)₃·xH₂O. Ketones are not affected under the reaction conditions. The highly catalytic nature of bismuth triflate and the fact that it is relatively non-toxic, easy to handle and insensitive to small amounts of air and moisture makes this procedure especially attractive for large-scale synthesis.

Original language	English (US)
Pages (from-to)	8133-8135
Number of pages	3
Journal	Tetrahedron Letters
Volume	42
Issue number	46
DOIs	https://doi.org/10.1016/S0040-4039(01)01756-7
State	Published - Nov 12 2001

Keywords

Acylals
Acylation
Bismuth and compounds
Protecting groups

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(01)01756-7

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title = "An efficient method for the chemoselective synthesis of acylals from aromatic aldehydes using bismuth triflate",

abstract = "Aromatic aldehydes are smoothly converted into the corresponding acylals in good yields in the presence of 0.10 mol% Bi(OTf)3·xH2O. Ketones are not affected under the reaction conditions. The highly catalytic nature of bismuth triflate and the fact that it is relatively non-toxic, easy to handle and insensitive to small amounts of air and moisture makes this procedure especially attractive for large-scale synthesis.",

keywords = "Acylals, Acylation, Bismuth and compounds, Protecting groups",

author = "Carrigan, {Marc D.} and Eash, {Kyle J.} and Oswald, {Matthew C.} and Mohan, {Ram S.}",

note = "Funding Information: The authors wish to acknowledge funding by the National Science Foundation (RUI grant). We also wish to thank Dr. C. Le Roux (CNRS, Universit{\'e} Paul-Sabatier) for useful comments on the synthesis of bismuth triflate.",

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T1 - An efficient method for the chemoselective synthesis of acylals from aromatic aldehydes using bismuth triflate

AU - Carrigan, Marc D.

AU - Eash, Kyle J.

AU - Oswald, Matthew C.

AU - Mohan, Ram S.

N1 - Funding Information: The authors wish to acknowledge funding by the National Science Foundation (RUI grant). We also wish to thank Dr. C. Le Roux (CNRS, Université Paul-Sabatier) for useful comments on the synthesis of bismuth triflate.

PY - 2001/11/12

Y1 - 2001/11/12

N2 - Aromatic aldehydes are smoothly converted into the corresponding acylals in good yields in the presence of 0.10 mol% Bi(OTf)3·xH2O. Ketones are not affected under the reaction conditions. The highly catalytic nature of bismuth triflate and the fact that it is relatively non-toxic, easy to handle and insensitive to small amounts of air and moisture makes this procedure especially attractive for large-scale synthesis.

AB - Aromatic aldehydes are smoothly converted into the corresponding acylals in good yields in the presence of 0.10 mol% Bi(OTf)3·xH2O. Ketones are not affected under the reaction conditions. The highly catalytic nature of bismuth triflate and the fact that it is relatively non-toxic, easy to handle and insensitive to small amounts of air and moisture makes this procedure especially attractive for large-scale synthesis.

KW - Acylals

KW - Acylation

KW - Bismuth and compounds

KW - Protecting groups

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 46

ER -

An efficient method for the chemoselective synthesis of acylals from aromatic aldehydes using bismuth triflate

Abstract

Keywords

ASJC Scopus subject areas

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