Mesoporous and hexagonally ordered CuAl-SBA-15-catalyzed tandem C-C and C-O bond formation between phenols and allylic alcohols

Shaji Varghese; Chokkalinkam Anand; Dattatray Dhawale; Ajayan Mano; Veerappan V. Balasubramanian; George Allen Gnana Raj; Samuthira Nagarajan; Mohammad A. Wahab; Ajayan Vinu

doi:10.1016/j.tetlet.2012.08.043

Mesoporous and hexagonally ordered CuAl-SBA-15-catalyzed tandem C-C and C-O bond formation between phenols and allylic alcohols

Shaji Varghese, Chokkalinkam Anand, Dattatray Dhawale, Ajayan Mano, Veerappan V. Balasubramanian, George Allen Gnana Raj, Samuthira Nagarajan, Mohammad A. Wahab, Ajayan Vinu

Chemical Engineering and Materials Science

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

8 Scopus citations

Abstract

A novel mesoporous catalyst, CuAl-SBA-15, with a hexagonally ordered porous structure prepared via a soft-templating approach in a highly acidic medium is used for tandem C-C and C-O bond formation between phenols and allylic alcohols to afford a variety of dihydrobenzopyrans in good yields. The catalyst is also found to be highly active for the synthesis of vitamin E and can be recycled several times without significant loss of its activity.

Original language	English (US)
Pages (from-to)	5656-5659
Number of pages	4
Journal	Tetrahedron Letters
Volume	53
Issue number	42
DOIs	https://doi.org/10.1016/j.tetlet.2012.08.043
State	Published - Oct 17 2012

Bibliographical note

Funding Information:
This work was financially supported by the Ministry of Education, Culture, Sports, Science, and Technology (MEXT) under the Strategic Program for Building an Asian Science and Technology Community Scheme and World Premier International Research Center (WPI) Initiative on Materials Nanoarchitectonics, MEXT, Japan. A.V. thanks the Australian Research Council for the award of a Future Fellowship. The authors also acknowledge the facilities, and the scientific and technical assistance, of the Australian Microscopy & Microanalysis Research Facility at the Centre for Microscopy and Microanalysis, University of Queensland.

Keywords

Chromans
Heterogeneous Catalyst
Mesoporous
Phenols
Tandem reactions

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10.1016/j.tetlet.2012.08.043

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title = "Mesoporous and hexagonally ordered CuAl-SBA-15-catalyzed tandem C-C and C-O bond formation between phenols and allylic alcohols",

abstract = "A novel mesoporous catalyst, CuAl-SBA-15, with a hexagonally ordered porous structure prepared via a soft-templating approach in a highly acidic medium is used for tandem C-C and C-O bond formation between phenols and allylic alcohols to afford a variety of dihydrobenzopyrans in good yields. The catalyst is also found to be highly active for the synthesis of vitamin E and can be recycled several times without significant loss of its activity.",

keywords = "Chromans, Heterogeneous Catalyst, Mesoporous, Phenols, Tandem reactions",

author = "Shaji Varghese and Chokkalinkam Anand and Dattatray Dhawale and Ajayan Mano and Balasubramanian, {Veerappan V.} and Raj, {George Allen Gnana} and Samuthira Nagarajan and Wahab, {Mohammad A.} and Ajayan Vinu",

note = "Funding Information: This work was financially supported by the Ministry of Education, Culture, Sports, Science, and Technology (MEXT) under the Strategic Program for Building an Asian Science and Technology Community Scheme and World Premier International Research Center (WPI) Initiative on Materials Nanoarchitectonics, MEXT, Japan. A.V. thanks the Australian Research Council for the award of a Future Fellowship. The authors also acknowledge the facilities, and the scientific and technical assistance, of the Australian Microscopy & Microanalysis Research Facility at the Centre for Microscopy and Microanalysis, University of Queensland. ",

year = "2012",

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doi = "10.1016/j.tetlet.2012.08.043",

language = "English (US)",

volume = "53",

pages = "5656--5659",

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T1 - Mesoporous and hexagonally ordered CuAl-SBA-15-catalyzed tandem C-C and C-O bond formation between phenols and allylic alcohols

AU - Varghese, Shaji

AU - Anand, Chokkalinkam

AU - Dhawale, Dattatray

AU - Mano, Ajayan

AU - Balasubramanian, Veerappan V.

AU - Raj, George Allen Gnana

AU - Nagarajan, Samuthira

AU - Wahab, Mohammad A.

AU - Vinu, Ajayan

N1 - Funding Information: This work was financially supported by the Ministry of Education, Culture, Sports, Science, and Technology (MEXT) under the Strategic Program for Building an Asian Science and Technology Community Scheme and World Premier International Research Center (WPI) Initiative on Materials Nanoarchitectonics, MEXT, Japan. A.V. thanks the Australian Research Council for the award of a Future Fellowship. The authors also acknowledge the facilities, and the scientific and technical assistance, of the Australian Microscopy & Microanalysis Research Facility at the Centre for Microscopy and Microanalysis, University of Queensland.

PY - 2012/10/17

Y1 - 2012/10/17

N2 - A novel mesoporous catalyst, CuAl-SBA-15, with a hexagonally ordered porous structure prepared via a soft-templating approach in a highly acidic medium is used for tandem C-C and C-O bond formation between phenols and allylic alcohols to afford a variety of dihydrobenzopyrans in good yields. The catalyst is also found to be highly active for the synthesis of vitamin E and can be recycled several times without significant loss of its activity.

AB - A novel mesoporous catalyst, CuAl-SBA-15, with a hexagonally ordered porous structure prepared via a soft-templating approach in a highly acidic medium is used for tandem C-C and C-O bond formation between phenols and allylic alcohols to afford a variety of dihydrobenzopyrans in good yields. The catalyst is also found to be highly active for the synthesis of vitamin E and can be recycled several times without significant loss of its activity.

KW - Chromans

KW - Heterogeneous Catalyst

KW - Mesoporous

KW - Phenols

KW - Tandem reactions

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JO - Tetrahedron Letters

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ER -

Mesoporous and hexagonally ordered CuAl-SBA-15-catalyzed tandem C-C and C-O bond formation between phenols and allylic alcohols

Abstract

Bibliographical note

Keywords

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