Facile ring-closure cyclization of arenes by nucleophilic C-alkylation reaction in ionic liquid

Dong Jin Hong; Dong Wook Kim; Dae Yoon Chi

doi:10.1016/j.tetlet.2009.10.065

Facile ring-closure cyclization of arenes by nucleophilic C-alkylation reaction in ionic liquid

Dong Jin Hong, Dong Wook Kim, Dae Yoon Chi

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Abstract

A novel synthetic method using an ionic liquid (IL) for a six-membered ring-closure cyclization is described. The ring-closure cyclization by nucleophilic C-alkylation was achieved with various halo- and alkanesulfonyloxyalkyl aromatic compounds in high yields with minimal byproducts using ILs as the reaction media in the absence of any catalyst. For example, the cyclization of 2-(3-methanesulfonyloxy-propoxy)naphthalene (1a) to 2,3-dihydro-1H-naphtho[2,1-b]pyran (2) in IL [bmim][PF₆] proceeded selectively at 150 °C for 24 h in 85% yield.

Original language	English
Pages (from-to)	54-56
Number of pages	3
Journal	Tetrahedron Letters
Volume	51
Issue number	1
DOIs	https://doi.org/10.1016/j.tetlet.2009.10.065
State	Published - 6 Jan 2010
Externally published	Yes

Bibliographical note

Funding Information:
This work was supported by research funds of Chonbuk National University in 2009, Nuclear Research and Development Program of the Korea Science and Engineering Foundation (KOSEF) grant funded by the Korean government (MEST) (Grant code: 2009-0078422 to D.W.K), and the conversing Research center program through the National Research Foundation of Korea (NRF) funded by MEST (Grant code: 2009-0081956 ).

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title = "Facile ring-closure cyclization of arenes by nucleophilic C-alkylation reaction in ionic liquid",

abstract = "A novel synthetic method using an ionic liquid (IL) for a six-membered ring-closure cyclization is described. The ring-closure cyclization by nucleophilic C-alkylation was achieved with various halo- and alkanesulfonyloxyalkyl aromatic compounds in high yields with minimal byproducts using ILs as the reaction media in the absence of any catalyst. For example, the cyclization of 2-(3-methanesulfonyloxy-propoxy)naphthalene (1a) to 2,3-dihydro-1H-naphtho[2,1-b]pyran (2) in IL [bmim][PF6] proceeded selectively at 150 °C for 24 h in 85% yield.",

author = "Hong, {Dong Jin} and Kim, {Dong Wook} and Chi, {Dae Yoon}",

note = "Funding Information: This work was supported by research funds of Chonbuk National University in 2009, Nuclear Research and Development Program of the Korea Science and Engineering Foundation (KOSEF) grant funded by the Korean government (MEST) (Grant code: 2009-0078422 to D.W.K), and the conversing Research center program through the National Research Foundation of Korea (NRF) funded by MEST (Grant code: 2009-0081956 ). ",

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doi = "10.1016/j.tetlet.2009.10.065",

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AU - Hong, Dong Jin

AU - Kim, Dong Wook

AU - Chi, Dae Yoon

N1 - Funding Information: This work was supported by research funds of Chonbuk National University in 2009, Nuclear Research and Development Program of the Korea Science and Engineering Foundation (KOSEF) grant funded by the Korean government (MEST) (Grant code: 2009-0078422 to D.W.K), and the conversing Research center program through the National Research Foundation of Korea (NRF) funded by MEST (Grant code: 2009-0081956 ).

PY - 2010/1/6

Y1 - 2010/1/6

N2 - A novel synthetic method using an ionic liquid (IL) for a six-membered ring-closure cyclization is described. The ring-closure cyclization by nucleophilic C-alkylation was achieved with various halo- and alkanesulfonyloxyalkyl aromatic compounds in high yields with minimal byproducts using ILs as the reaction media in the absence of any catalyst. For example, the cyclization of 2-(3-methanesulfonyloxy-propoxy)naphthalene (1a) to 2,3-dihydro-1H-naphtho[2,1-b]pyran (2) in IL [bmim][PF6] proceeded selectively at 150 °C for 24 h in 85% yield.

AB - A novel synthetic method using an ionic liquid (IL) for a six-membered ring-closure cyclization is described. The ring-closure cyclization by nucleophilic C-alkylation was achieved with various halo- and alkanesulfonyloxyalkyl aromatic compounds in high yields with minimal byproducts using ILs as the reaction media in the absence of any catalyst. For example, the cyclization of 2-(3-methanesulfonyloxy-propoxy)naphthalene (1a) to 2,3-dihydro-1H-naphtho[2,1-b]pyran (2) in IL [bmim][PF6] proceeded selectively at 150 °C for 24 h in 85% yield.

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Facile ring-closure cyclization of arenes by nucleophilic C-alkylation reaction in ionic liquid

Abstract

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