Fig. 2: Screening of NHC preligands for mechanochemical iron-catalyzed hydroarylation of unactivated alkenes. | Nature Communications

Fig. 2: Screening of NHC preligands for mechanochemical iron-catalyzed hydroarylation of unactivated alkenes.

From: Mechanochemical ligand-controlled regiodivergent hydroarylation of alkenes via iron-catalyzed C−H activation

Fig. 2: Screening of NHC preligands for mechanochemical iron-catalyzed hydroarylation of unactivated alkenes.The alternative text for this image may have been generated using AI.

Reaction conditions: 1a (0.1 mmol), 2a (0.15 mmol), Fe(acac)3 (10 mol%), NHC preligand (10 mol%), Mg chip (50 mol%), TMEDA (0.1 mmol) and THF (50 μL) were placed in a stainless-steel vessel (5 mL) with stainless-steel ball (dMB = 7 mm), milled in a mixer mill (RETSCH MM 400) at 30 Hz for 180 min under nitrogen atmosphere. Then THF (3 mL) and HCl aq. (3 M, 1 mL) were added, and the mixture was stirred for 2 h. The ratio of l:b is > 99:1 for all cases. The yield was determined by 1H NMR spectroscopy using 1,3,5-trimethoxybenzene as the internal standard. aIn the absence of TMEDA: 72% yield; in the absence of THF: 83% yield; in the absence of Fe(acac)3, NHC preligand, or Mg chip: n.d. TMEDA, N,N,N’,N’-tetramethylethylenediamine; THF, tetrahydrofuran; Mes, 2,4,6-trimethylphenyl; Dipp, 2,6-diisopropylphenyl; Xyl, 2,6-dimethylphenyl; n.d., not detected.

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