Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2016, Issue 32, Pages 5340-5344Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201600987
Keywords
Ball milling; Chemoselectivity; Cross-coupling; Mannich reaction; Mechanical properties
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Funding
- Special Program for Key Basic Research of the Ministry of Science and Technology of China [2014CB460608]
- National Natural Science Foundation of China [21406201, 21506190, 21376221]
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A mechanochemical oxidative Mannich reaction of N-tert-butoxycarbonyl (Boc) tetrahydroquinolines and ketones was successfully developed under solvent-free ball-milling conditions. The reaction afforded the desired coupling products in satisfactory yields under mild and tractable oxidative conditions. Side reactions such as deprotection of the Boc group were prevented by carefully adjusting the milling parameters, including milling frequency, time, milling-ball filling degree, milling-ball size, and grinding auxiliary. Further examination of the scope indicated that the reaction system could also be applied to the N-benzyloxycarbonyl and N-aryl substrates to afford the corresponding products in moderate to good yields.
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