Fig. 2: Mechanochemical generation of organolithium species. | Nature Synthesis

Fig. 2: Mechanochemical generation of organolithium species.

From: Mechanochemical activation of metallic lithium for the generation and application of organolithium compounds in air

Fig. 2

a, Optimization study for the formation of organolithium reagents. Conditions: 1 (1.0 mmol), Li (2.2 mmol) and additive (2.2 mmol) in a stainless steel ball-milling jar (10 ml) with two stainless steel balls (10 mm). Gas-chromatography (GC) yields are shown. The photos show that lithium metal was completely pulverized under mechanochemical conditions, while some remains unreacted in the test tube reaction. aReactions were carried out in a test tube with a stirring bar. b, Deuterium-labelling experiment. Conditions: 1 (1.0 mmol), Li (2.2 mmol), Et2O (2.2 mmol) and D2O (5.0 mmol) in a stainless steel ball-milling jar (10 ml) with two stainless steel balls (10 mm). Integrated 1H NMR spectroscopic yields are shown. THF, tetrahydrofuran; MTBE, tert-butyl methyl ether; TMEDA, tetramethylenediamine.

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