Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 22, Pages 6294-6297Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201612235
Keywords
amines; diazo compounds; flow chemistry; esterification; synthetic methods
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Funding
- Natural Science and Engineering Research Council of Canada (NSERC)
- NSERC (Canada)
- Canada Foundation for Innovation
- Canada Research Chair Program
- Universite de Montreal
- Centre in Green Chemistry and Catalysis (CGCC)
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A 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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