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Expedient Organocatalytic Aza-Morita–Baylis–Hillman Reaction through Ball-Milling

Matthew T. J. Williams,Louis C. Morrill,D. Browne

2020 · DOI: 10.1021/acssuschemeng.0c07320
ACS Sustainable Chemistry and Engineering · 18 Citations

TLDR

A ball-milling enabled tertiary amine catalyzed aza-Morita–Baylis–Hillman reaction is reported and a 12-fold scaled-up example is reported as well as experimental comparisons to solution-based experiments and neat-stirred reactions.

Abstract

A ball-milling enabled tertiary amine catalyzed aza-Morita–Baylis–Hillman reaction is reported. The reaction process does not require solvent, has significantly shorter reaction times than previous methods and is reported on a range of imines and acrylate Michael acceptors across than 26 examples. A 12-fold scaled-up example is also reported as well as experimental comparisons to solution-based experiments and neat-stirred reactions.