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Direct Exploitation of the Ethynyl Moiety in Calcium Carbide Through Sealed Ball Milling
Author(s) -
Hosseini Abolfazl,
Schreiner Peter R.
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000612
Subject(s) - moiety , chemistry , aryl , ball mill , calcium carbide , mechanochemistry , electrophile , halide , carbide , combinatorial chemistry , catalysis , organic chemistry , chemical engineering , alkyl , engineering
Ball milling of calcium carbide (CaC 2 ) enables the reaction of its ethynyl moiety with organic electrophiles. This was realized simply by co‐milling CaC 2 with organic substrates in a sealed jar without the need for an additive or a catalyst. Various ketones including those bearing α‐hydrogens were ethynylated in good yields at short reaction times. Aryl halides are also amenable substrates for this protocol as they furnish aryl ethynes through a benzyne intermediate. This method offers a practical and cheap alternative to the established procedures for introducing ethynyl functionalities.