Synthesis
GENERAL STEPS: In a glove box, [3a] + [BArF4] (1.0 mol%) and Me2PhSiH(2a) (2.1 or 5.0 eq.) were added sequentially to a flame-dried GLC vial equipped with a magnetic stir bar. For solid feedstocks, the indicated nitrile was added to the glove box; for liquid feedstocks, it was added via a microsyringe outside the glove box. The reaction mixture was stirred at room temperature for the indicated time. Upon completion of the reaction, the reaction was quenched with a mixture of cyclohexane and tert-butyl methyl ether (90:10, 0.5 mL) containing 4% Et3N. The resulting solution was filtered through a diatomaceous earth pad coated with a small amount of silica gel, and the same ratio of cyclohexane to tert-butyl methyl ether (containing 4% Et3N, 3-4 mL) was used as the eluent. The solvent was removed by concentration under reduced pressure and the residue was dissolved in Et2O (1 mL), followed by the addition of a solution of Et2O (1.0 mL, 2.0 mmol, 10 equiv.) in 2M HCl. The resulting suspension was stirred for 1 h and filtered to give (2-chlorophenyl)formamide hydrochloride as a white to yellow solid.
References
[1] Synlett, 2017, vol. 28, # 18, p. 2411 - 2414
[2] Journal of the American Chemical Society, 2016, vol. 138, # 28, p. 8781 - 8788
[3] Journal of the American Chemical Society, 2016, vol. 138, # 28, p. 8809 - 8814
[4] Journal of Organic Chemistry, 2015, vol. 80, # 14, p. 7281 - 7287
[5] Catalysis Science and Technology, 2018, vol. 8, # 2, p. 499 - 507
