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Synthesis of 2,6-Hexa-tert-butylterphenyl Derivatives, 2,6-(2,4,6‑t‑Bu3C6H2)2­C6H3X, where X = I, Li, OH, SH, N3, or NH2

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posted on 01.05.2017, 14:19 authored by Konstantin V. Bukhryakov, Richard R. Schrock, Amir H. Hoveyda, Peter Müller, Jonathan Becker
A “double benzyne” reaction between 1,3-dichloro-2-iodobenzene and 2,4,6-t-Bu3C6H2MgBr followed by the addition of iodine led to 2,6-(2,4,6-t-Bu3C6H2)2C6H3I (HTBTI) in 65% yield. Lithiation of HTBTI with Li-t-Bu gave Li­(Et2O)2HTBT from which HTBTSH, HTBTN3, HTBTNH2, and HTBTOH were prepared. An X-ray structure of W­(OHTBT)2Cl4 shows that the two HTBTO ligands are trans to one another with the t-Bu3C6H2 groups on one HTBTO interdigitated with the t-Bu3C6H2 groups on the other HTBTO.

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