Environment-friendly organic synthesis using bismuth compounds. Bismuth triflate catalyzed synthesis of substituted 3,4-dihydro-2H-1-benzopyrans

Mai P. Nguyen; Joshua N. Arnold; Katherine E. Peterson; Ram S. Mohan

doi:10.1016/j.tetlet.2004.10.118

Environment-friendly organic synthesis using bismuth compounds. Bismuth triflate catalyzed synthesis of substituted 3,4-dihydro-2H-1-benzopyrans

Mai P. Nguyen, Joshua N. Arnold, Katherine E. Peterson, Ram S. Mohan

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

18 Scopus citations

Abstract

A highly catalytic method for the synthesis of dihydrobenzopyrans from salicylaldehydes has been developed. An extension of this method to the synthesis of a pyrano[2,3,b]benzopyran has also been achieved. Bi(OTf) ₃•xH ₂O (1 < x < 4) (0.1 mol%) smoothly catalyzes the condensation of substituted salicylaldehydes with 2,2-dimethoxypropane to give the corresponding substituted 3,4-dihydro-2H-1- benzopyrans as a mixture of diastereomers (9:1) in moderate yields. The relative configuration of the methoxy groups in the two diastereomers was established by NOE experiments. The advantages of this method include the use of an easy to handle, inexpensive and relatively non-toxic catalyst.

Original language	English (US)
Pages (from-to)	9369-9371
Number of pages	3
Journal	Tetrahedron Letters
Volume	45
Issue number	51
DOIs	https://doi.org/10.1016/j.tetlet.2004.10.118
State	Published - Dec 13 2004
Externally published	Yes

Bibliographical note

Funding Information:
We gratefully acknowledge funding from the National Science Foundation (RUI grant # 0350216). R.S.M. is also indebted to The Camille Henry Dreyfus foundation for a Henry Dreyfus Teacher Scholar award.

Keywords

Bismuth and compounds
Bismuth triflate
Dihydrobenzopyrans
Green chemistry

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title = "Environment-friendly organic synthesis using bismuth compounds. Bismuth triflate catalyzed synthesis of substituted 3,4-dihydro-2H-1-benzopyrans",

abstract = "A highly catalytic method for the synthesis of dihydrobenzopyrans from salicylaldehydes has been developed. An extension of this method to the synthesis of a pyrano[2,3,b]benzopyran has also been achieved. Bi(OTf) 3•xH 2O (1 < x < 4) (0.1 mol%) smoothly catalyzes the condensation of substituted salicylaldehydes with 2,2-dimethoxypropane to give the corresponding substituted 3,4-dihydro-2H-1- benzopyrans as a mixture of diastereomers (9:1) in moderate yields. The relative configuration of the methoxy groups in the two diastereomers was established by NOE experiments. The advantages of this method include the use of an easy to handle, inexpensive and relatively non-toxic catalyst.",

keywords = "Bismuth and compounds, Bismuth triflate, Dihydrobenzopyrans, Green chemistry",

author = "Nguyen, {Mai P.} and Arnold, {Joshua N.} and Peterson, {Katherine E.} and Mohan, {Ram S.}",

note = "Funding Information: We gratefully acknowledge funding from the National Science Foundation (RUI grant # 0350216). R.S.M. is also indebted to The Camille Henry Dreyfus foundation for a Henry Dreyfus Teacher Scholar award. ",

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AU - Nguyen, Mai P.

AU - Arnold, Joshua N.

AU - Peterson, Katherine E.

AU - Mohan, Ram S.

N1 - Funding Information: We gratefully acknowledge funding from the National Science Foundation (RUI grant # 0350216). R.S.M. is also indebted to The Camille Henry Dreyfus foundation for a Henry Dreyfus Teacher Scholar award.

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Y1 - 2004/12/13

N2 - A highly catalytic method for the synthesis of dihydrobenzopyrans from salicylaldehydes has been developed. An extension of this method to the synthesis of a pyrano[2,3,b]benzopyran has also been achieved. Bi(OTf) 3•xH 2O (1 < x < 4) (0.1 mol%) smoothly catalyzes the condensation of substituted salicylaldehydes with 2,2-dimethoxypropane to give the corresponding substituted 3,4-dihydro-2H-1- benzopyrans as a mixture of diastereomers (9:1) in moderate yields. The relative configuration of the methoxy groups in the two diastereomers was established by NOE experiments. The advantages of this method include the use of an easy to handle, inexpensive and relatively non-toxic catalyst.

AB - A highly catalytic method for the synthesis of dihydrobenzopyrans from salicylaldehydes has been developed. An extension of this method to the synthesis of a pyrano[2,3,b]benzopyran has also been achieved. Bi(OTf) 3•xH 2O (1 < x < 4) (0.1 mol%) smoothly catalyzes the condensation of substituted salicylaldehydes with 2,2-dimethoxypropane to give the corresponding substituted 3,4-dihydro-2H-1- benzopyrans as a mixture of diastereomers (9:1) in moderate yields. The relative configuration of the methoxy groups in the two diastereomers was established by NOE experiments. The advantages of this method include the use of an easy to handle, inexpensive and relatively non-toxic catalyst.

KW - Bismuth and compounds

KW - Bismuth triflate

KW - Dihydrobenzopyrans

KW - Green chemistry

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Environment-friendly organic synthesis using bismuth compounds. Bismuth triflate catalyzed synthesis of substituted 3,4-dihydro-2H-1-benzopyrans

Abstract

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Keywords

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