A facile and efficient method for the rearrangement of aryl-substituted epoxides to aldehydes and ketones using bismuth triflate

Kaushik A. Bhatia; Kyle J. Eash; Nicholas M. Leonard; Matthew C. Oswald; Ram S. Mohan

doi:10.1016/S0040-4039(01)01519-2

A facile and efficient method for the rearrangement of aryl-substituted epoxides to aldehydes and ketones using bismuth triflate

Kaushik A. Bhatia, Kyle J. Eash, Nicholas M. Leonard, Matthew C. Oswald, Ram S. Mohan

Physical Medicine and Rehabilitation

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

107 Scopus citations

Abstract

Aryl-substituted epoxides undergo smooth rearrangement in the presence of 0.01-0.1 mol% Bi(OTf)₃·xH₂O. The rearrangement is regioselective with aryl-substituted epoxides, and products arise from cleavage of the benzylic C-O bond. The highly catalytic nature of this method coupled with the fact that the reagent is relatively non-toxic, easy to handle and inexpensive make it an attractive alternative to more corrosive and toxic Lewis acids, such as BF₃·Et₂O, currently used to effect epoxide rearrangements.

Original language	English (US)
Pages (from-to)	8129-8132
Number of pages	4
Journal	Tetrahedron Letters
Volume	42
Issue number	46
DOIs	https://doi.org/10.1016/S0040-4039(01)01519-2
State	Published - Nov 12 2001

Keywords

Bismuth and compounds
Epoxides
Rearrangements

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/S0040-4039(01)01519-2

Cite this

@article{ce73ece5f9874474ac6feec54cea6d7c,

title = "A facile and efficient method for the rearrangement of aryl-substituted epoxides to aldehydes and ketones using bismuth triflate",

abstract = "Aryl-substituted epoxides undergo smooth rearrangement in the presence of 0.01-0.1 mol% Bi(OTf)3·xH2O. The rearrangement is regioselective with aryl-substituted epoxides, and products arise from cleavage of the benzylic C-O bond. The highly catalytic nature of this method coupled with the fact that the reagent is relatively non-toxic, easy to handle and inexpensive make it an attractive alternative to more corrosive and toxic Lewis acids, such as BF3·Et2O, currently used to effect epoxide rearrangements.",

keywords = "Bismuth and compounds, Epoxides, Rearrangements",

author = "Bhatia, {Kaushik A.} and Eash, {Kyle J.} and Leonard, {Nicholas M.} 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 Professor C. Le Roux (CNRS, Universit{\'e} Paul-Sabatier) for useful comments on the synthesis of bismuth triflate. ",

year = "2001",

month = nov,

day = "12",

doi = "10.1016/S0040-4039(01)01519-2",

language = "English (US)",

volume = "42",

pages = "8129--8132",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "46",

}

TY - JOUR

T1 - A facile and efficient method for the rearrangement of aryl-substituted epoxides to aldehydes and ketones using bismuth triflate

AU - Bhatia, Kaushik A.

AU - Eash, Kyle J.

AU - Leonard, Nicholas M.

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 Professor 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 - Aryl-substituted epoxides undergo smooth rearrangement in the presence of 0.01-0.1 mol% Bi(OTf)3·xH2O. The rearrangement is regioselective with aryl-substituted epoxides, and products arise from cleavage of the benzylic C-O bond. The highly catalytic nature of this method coupled with the fact that the reagent is relatively non-toxic, easy to handle and inexpensive make it an attractive alternative to more corrosive and toxic Lewis acids, such as BF3·Et2O, currently used to effect epoxide rearrangements.

AB - Aryl-substituted epoxides undergo smooth rearrangement in the presence of 0.01-0.1 mol% Bi(OTf)3·xH2O. The rearrangement is regioselective with aryl-substituted epoxides, and products arise from cleavage of the benzylic C-O bond. The highly catalytic nature of this method coupled with the fact that the reagent is relatively non-toxic, easy to handle and inexpensive make it an attractive alternative to more corrosive and toxic Lewis acids, such as BF3·Et2O, currently used to effect epoxide rearrangements.

KW - Bismuth and compounds

KW - Epoxides

KW - Rearrangements

UR - http://www.scopus.com/inward/record.url?scp=0035851385&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0035851385&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(01)01519-2

DO - 10.1016/S0040-4039(01)01519-2

M3 - Article

AN - SCOPUS:0035851385

SN - 0040-4039

VL - 42

SP - 8129

EP - 8132

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 46

ER -

A facile and efficient method for the rearrangement of aryl-substituted epoxides to aldehydes and ketones using bismuth triflate

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this