Convenient synthesis of organic-electronics-oriented building blocks via on-water and under-air homocoupling of (hetero)aryl iodides

Yi An Chen, Ching Yuan Liu

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

We report herein an operationally simple homocoupling reaction that targets the convenient synthesis of organic-electronically important building blocks. A variety of synthetically useful bithiophene derivatives and functionalized biphenyls are efficiently prepared by an on-water and under-air protocol using Pd/C as catalyst. We find that Pd/C gives generally higher and cleaner homocoupling conversions than using Pd(OAc)2 in the cases of (hetero)aryl iodides since Pd(OAc)2 triggers more side reactions including dehalogenations and oligomerizations. Under the optimum conditions, a broad range of functional groups such as ester, ketone, aldehyde, nitrile, nitro, chloride, and bromide are well tolerated. We expect the present methodology would make a valuable synthetic contribution towards bridging green chemistry with thiophene-based organic materials.

Original languageEnglish
Pages (from-to)74180-74188
Number of pages9
JournalRSC Advances
Volume5
Issue number91
DOIs
StatePublished - 25 Aug 2015

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