Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 33, Pages 10718-10722Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201805505
Keywords
alkynes; amines; calcium carbide; 1,4-diamino-2-butynes; mechanochemistry
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Funding
- RWTH Aachen University through the RWTH Start-up grant [StUpPD_221-16]
- German Federal Government
- German State Government
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The ability of mechanochemistry to alter established chemical selectivity is demonstrated. A copper(I)-catalyzed mechanochemical aldehyde/alkyne/amine coupling using calcium carbide as the acetylene source provides selective access to 1,4-diamino-2-butynes, which contrasts classical approaches that provide propargylamine-type products. Solventless milling conditions were found to be essential to unmask A(3) coupling products with new compositions.
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