A Mild and Convenient Synthesis of 1,2,3-Triiodoarenes via Consecutive Iodination/Diazotization/Iodination Strategy

Raed M. Al-Zoubi; Hassan Abul Futouh; Robert McDonald

doi:10.1071/CH13324

RESEARCH ARTICLE

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A Mild and Convenient Synthesis of 1,2,3-Triiodoarenes via Consecutive Iodination/Diazotization/Iodination Strategy

Raed M. Al-Zoubi ^A ^C , Hassan Abul Futouh ^A and Robert McDonald ^B

+ Author Affiliations

- Author Affiliations

^A Department of Chemistry, Jordan University of Science and Technology, PO Box 3030, Irbid, 22110, Jordan.

^B Department of Chemistry, Gunning-Lemieux Chemistry Centre, University of Alberta, Edmonton, Alberta, T6G2G2, Canada.

^C Corresponding author. Email: rmzoubi@just.edu.jo

Australian Journal of Chemistry 66(12) 1570-1575 https://doi.org/10.1071/CH13324
Submitted: 25 June 2013 Accepted: 20 August 2013 Published: 25 September 2013

Abstract

A mild and convenient synthesis of 1,2,3-triiodoarenes has been developed. This method consists of two steps which can be performed on multigram scale with moderate to excellent yields. This report discloses a practical synthesis of 1,2,3-triiodoarenes and 1,2,3-trihaloarenes that is general in scope, operationally simple, scalable, and is easy to workup and to purify. We also report the first regioselective transmetalation reaction of 1,2,3-triiodoarenes to provide ortho-diiodoaryl derivatives, which are useful building blocks and indeed are hard to make by other means.

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A Mild and Convenient Synthesis of 1,2,3-Triiodoarenes via Consecutive Iodination/Diazotization/Iodination Strategy

Abstract

References

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