Rhodium-catalyzed one-pot hydroformylation-cyclization of allylbenzene derivatives: Simple and efficient route to 5,6-dihydronaphthalenes

Mouheddin Alhaffar; Rami Suleiman; Bassam El Ali

doi:10.1016/j.catcom.2010.02.014

Rhodium-catalyzed one-pot hydroformylation-cyclization of allylbenzene derivatives: Simple and efficient route to 5,6-dihydronaphthalenes

Mouheddin Alhaffar
, Rami Suleiman
, Bassam El Ali^*

^*Corresponding author for this work

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

13 Scopus citations

Abstract

The one-pot hydroformylation-cyclization of allylbenzene derivatives by the catalyst system Rh(CO)₂acac/ultranox626/CO/H₂/CH₂Cl₂ led chemoselectively to 5,6-dihydronaphthalene derivatives 5a-d in good yields. The addition of a catalytic amount of H₃PO₄ enhanced in situ the cyclization process via the nucleophilic attack on the carbonyl group of the linear aldehyde, and finally the elimination of alcohol. The type of substitution on phenyl group of the allylbenzene is of great importance in enhancing the cyclization process.

Original language	English
Pages (from-to)	778-782
Number of pages	5
Journal	Catalysis Communications
Volume	11
Issue number	8
DOIs	https://doi.org/10.1016/j.catcom.2010.02.014
State	Published - 31 Mar 2010

Bibliographical note

Funding Information:
We thank King Fahd University of Petroleum and Minerals (KFUPM-Saudi Arabia) for providing all support to this project. This project has been funded by King Fahd University of Petroleum and Minerals under Project No. IN070379.

Keywords

Allylbenzene
Cyclization
Dihydronaphthalenes
Eugenol
Hydroformylation
Phosphite
Rhodium
Ultranox626

ASJC Scopus subject areas

Catalysis
General Chemistry
Process Chemistry and Technology

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10.1016/j.catcom.2010.02.014

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title = "Rhodium-catalyzed one-pot hydroformylation-cyclization of allylbenzene derivatives: Simple and efficient route to 5,6-dihydronaphthalenes",

abstract = "The one-pot hydroformylation-cyclization of allylbenzene derivatives by the catalyst system Rh(CO)2acac/ultranox626/CO/H2/CH2Cl2 led chemoselectively to 5,6-dihydronaphthalene derivatives 5a-d in good yields. The addition of a catalytic amount of H3PO4 enhanced in situ the cyclization process via the nucleophilic attack on the carbonyl group of the linear aldehyde, and finally the elimination of alcohol. The type of substitution on phenyl group of the allylbenzene is of great importance in enhancing the cyclization process.",

keywords = "Allylbenzene, Cyclization, Dihydronaphthalenes, Eugenol, Hydroformylation, Phosphite, Rhodium, Ultranox626",

author = "Mouheddin Alhaffar and Rami Suleiman and Ali, \{Bassam El\}",

note = "Funding Information: We thank King Fahd University of Petroleum and Minerals (KFUPM-Saudi Arabia) for providing all support to this project. This project has been funded by King Fahd University of Petroleum and Minerals under Project No. IN070379.",

year = "2010",

month = mar,

day = "31",

doi = "10.1016/j.catcom.2010.02.014",

language = "English",

volume = "11",

pages = "778--782",

journal = "Catalysis Communications",

issn = "1566-7367",

publisher = "Elsevier B.V.",

number = "8",

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TY - JOUR

T1 - Rhodium-catalyzed one-pot hydroformylation-cyclization of allylbenzene derivatives

T2 - Simple and efficient route to 5,6-dihydronaphthalenes

AU - Alhaffar, Mouheddin

AU - Suleiman, Rami

AU - Ali, Bassam El

N1 - Funding Information: We thank King Fahd University of Petroleum and Minerals (KFUPM-Saudi Arabia) for providing all support to this project. This project has been funded by King Fahd University of Petroleum and Minerals under Project No. IN070379.

PY - 2010/3/31

Y1 - 2010/3/31

N2 - The one-pot hydroformylation-cyclization of allylbenzene derivatives by the catalyst system Rh(CO)2acac/ultranox626/CO/H2/CH2Cl2 led chemoselectively to 5,6-dihydronaphthalene derivatives 5a-d in good yields. The addition of a catalytic amount of H3PO4 enhanced in situ the cyclization process via the nucleophilic attack on the carbonyl group of the linear aldehyde, and finally the elimination of alcohol. The type of substitution on phenyl group of the allylbenzene is of great importance in enhancing the cyclization process.

AB - The one-pot hydroformylation-cyclization of allylbenzene derivatives by the catalyst system Rh(CO)2acac/ultranox626/CO/H2/CH2Cl2 led chemoselectively to 5,6-dihydronaphthalene derivatives 5a-d in good yields. The addition of a catalytic amount of H3PO4 enhanced in situ the cyclization process via the nucleophilic attack on the carbonyl group of the linear aldehyde, and finally the elimination of alcohol. The type of substitution on phenyl group of the allylbenzene is of great importance in enhancing the cyclization process.

KW - Allylbenzene

KW - Cyclization

KW - Dihydronaphthalenes

KW - Eugenol

KW - Hydroformylation

KW - Phosphite

KW - Rhodium

KW - Ultranox626

UR - https://www.scopus.com/pages/publications/77949489158

U2 - 10.1016/j.catcom.2010.02.014

DO - 10.1016/j.catcom.2010.02.014

M3 - Article

AN - SCOPUS:77949489158

SN - 1566-7367

VL - 11

SP - 778

EP - 782

JO - Catalysis Communications

JF - Catalysis Communications

IS - 8

ER -

Rhodium-catalyzed one-pot hydroformylation-cyclization of allylbenzene derivatives: Simple and efficient route to 5,6-dihydronaphthalenes

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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