Abstract
AbstractA novel synthesis of trimethylsilyldiazomethane (TMSCHN2) by diazotization of trimethylsilylmethylamine (TMSCH2NH2) is reported using batch and continuous flow synthesis. The latter affords a daily production of 275 g (2.4 mol) of TMSCHN2. Other silylated methylamines were also successfully reacted under the developed reaction conditions to furnish various silicon‐bearing diazomethane reagents. The applicability of the process is highlighted by disclosure of batch and continuous flow one‐pot esterification and 1,3‐dipolar cycloaddition processes. Furthermore, the high‐yielding esterification of carboxylic acids with silylated and substituted methylamines in continuous flow is disclosed. Finally, work‐up and purification procedures are reported for the preparation of a 2‐MeTHF solution of TMSCHN2, which can be used in rhodium‐catalyzed methylenation and homologation reactions.
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