An expedient approach to ferrocenyl thioamides via Fischer carbenes

Oxidative demetalation of Fischer ferrocenyl ethoxy carbene complexes (1a–c, M = Cr, Mo, W) and new Fischer ferrocenyl R-amino carbene complexes [2–5 (a–c), 11–15 (a–c), and 21–22 (a–c); M = Cr, Mo, W; R = H, CH3, C2H5, C3H7, (CH2)2OH, (CH2)3OH, (CH2)2(OMe)2, (CH2)3N(Me)2, CH2CHCH2, (CH2)2OSi(CH3)3, (CH2)3OSi(CH3)3] with elemental sulfur–NaBH4 were carried out under mild conditions, obtaining O-ethyl ferrocenecarbothioate (6) and novel ferrocenyl thioamides (7–10 and 16–20) in excellent yields.

Graphical abstractAn efficient route to easily access a diversity of new potential ferrocenyl thiomides was achieved in high overall yields. The scope of method was evidenced by the tolerance to different functional groups on side chain of amino ferrocenyl carbene.Figure optionsDownload full-size imageDownload as PowerPoint slide