Synthesis of Multisubstituted Aromatics via 3‑Triazenylarynes

An efficient method for generating 3-triazenylarynes from ortho-iodoaryl triflate-type precursors was developed. The generated arynes reacted with various arynophiles with high regioselectivity because of the triazenyl group. The 3-triazenylaryne precursors functioned as useful intermediates of dive...

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Bibliographic Details
Published inOrganic letters Vol. 25; no. 38; pp. 7030 - 7034
Main Authors Taguchi, Jumpei, Okuyama, Takumi, Tomita, Satomi, Niwa, Takashi, Hosoya, Takamitsu
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 29.09.2023
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
TRIAZENES
REGIOSELECTIVE DIELS-ALDER
ARYLTRIAZENES
ACTIVATION
CROSS-COUPLING REACTION
EFFICIENT GENERATION
1-ARYLTRIAZENES
SELECTIVE SYNTHESIS
3-BORYLBENZYNES
ARYNE DISTORTIONS
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Summary:An efficient method for generating 3-triazenylarynes from ortho-iodoaryl triflate-type precursors was developed. The generated arynes reacted with various arynophiles with high regioselectivity because of the triazenyl group. The 3-triazenylaryne precursors functioned as useful intermediates of diverse multisubstituted aromatic compounds through the transformation of the remaining triazenyl group of aryne adducts and triazenyl group-directed ortho-C–H functionalization.
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.3c02615