Unusual Regio- and Chemoselectivity in Oxidation of Pyrroles and Indoles Enabled by a Thianthrenium Salt Intermediate,Angewandte Chemie International Edition

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Unusual Regio- and Chemoselectivity in Oxidation of Pyrroles and Indoles Enabled by a Thianthrenium Salt Intermediate
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2024-06-03 , DOI: 10.1002/anie.202405057
Jodie L Hann ₁ , Catherine L Lyall ₂ , Gabriele Kociok-Köhn ₂ , Chiara Faverio ₁ , G Dan Pantoş ₁ , Simon E Lewis _{1,

3}

Affiliation

TTSO (thianthrene-S-oxide) in conjunction with TFAA (trifluoroacetic anhydride) and Brønsted acid is able to oxidize pyrroles to Δ³-pyrrol-2-ones and indoles to indolin-3-ones via a thianthrenium salt intermediate. In the case of 3-substituted pyrroles, the product isomer formed is that in which oxygenation has been introduced at the more sterically hindered position.

中文翻译：

铊盐中间体实现吡咯和吲哚氧化过程中异常的区域选择性和化学选择性

TTSO（噻蒽-S-氧化物）与 TFAA（三氟乙酸酐）和布朗斯台德酸结合，能够通过铊盐中间体将吡咯氧化为 Δ ³ -吡咯-2-酮，将吲哚氧化为吲哚啉-3-酮。在3-取代吡咯的情况下，形成的产物异构体是其中在空间位阻更大的位置引入氧化的产物异构体。

更新日期：2024-06-03

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