Institut für Organische und Biomolekulare Chemie Georg-August-Universität Göttingen Tammannstr 2, 37073 Göttingen, Germany.
Org Biomol Chem. 2021 Apr 7;19(13):2941-2948. doi: 10.1039/d1ob00285f. Epub 2021 Mar 16.
The one-pot synthesis of well-defined 5-(diarylimino) and 5-(sulfoximido)dibenzothiophenium triflates, respectively from diarylimines or sulfoximines, is reported and the structures of a series of these compounds are elucidated by X-ray crystallography. In analogy to their hypervalent I(iii) analogues, the iminoyl and sulfoximidoyl groups of these compounds can be selectively transferred to organic substrates. Specifically, the uncatalyzed imination of thiols or sulfinates proceeds with good yields, while under the mild reaction conditions offered by visible light photoredox catalysis, the radical amination of hydrazones or the sulfoximidation of benzylic, allylic and propargylic C-H bonds takes place satisfactorily.
本文报道了分别由二芳基胺或亚磺酰胺一锅法合成结构明确的 5-（二芳基亚氨基）和 5-（亚磺酰亚氨基）二苯并噻吩𬭩三氟甲磺酸酯，并通过 X 射线晶体学阐明了一系列此类化合物的结构。与它们的高价态 I(iii)类似物类似，这些化合物的亚氨酰基和亚磺酰亚氨酰基可以选择性地转移到有机底物上。具体而言，硫醇或亚磺酸盐的无催化亚胺化反应以良好的收率进行，而在可见光光氧化还原催化提供的温和反应条件下，腙的自由基胺化或苄基、烯丙基和炔丙基 C-H 键的亚磺酰亚胺化反应也能令人满意地进行。
