Selective Halogen-Lithium Exchange of 1,2-Dihaloarenes for Successive [2+4] Cycloadditions of Arynes and Isobenzofurans

Shohei Eda; Toshiyuki Hamura

doi:10.3390/molecules201019449

Selective Halogen-Lithium Exchange of 1,2-Dihaloarenes for Successive [2+4] Cycloadditions of Arynes and Isobenzofurans

Molecules. 2015 Oct 23;20(10):19449-62. doi: 10.3390/molecules201019449.

Authors

Shohei Eda¹, Toshiyuki Hamura²

Affiliations

¹ Department of Applied Chemistry for Environment, School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo 669-1337, Japan. shoheie816@gmail.com.
² Department of Applied Chemistry for Environment, School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo 669-1337, Japan. thamura@kwansei.ac.jp.

Abstract

Successive [2+4] cycloadditions of arynes and isobenzofurans by site-selective halogen-lithium exchange of 1,2-dihaloarenes were developed, allowing the rapid construction of polycyclic compounds which serve as a useful synthetic intermediates for the preparation of various polyacene derivatives.

Keywords: 1,2-dihaloarenes; [2+4] cycloaddition; aryne; halogen-lithium exchange; isobenzofuran; polyacene.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Benzofurans / chemistry*
Bromides / chemistry
Catalysis
Cycloaddition Reaction
Iodides / chemistry
Lithium / chemistry*
Polycyclic Compounds / chemical synthesis*

Substances

Benzofurans
Bromides
Iodides
Polycyclic Compounds
Lithium
iodobromine
benzofuran