A direct synthesis of allenes by a traceless Petasis reaction |
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| Authors: | Mundal Devon A Lutz Kelly E Thomson Regan J |
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| Institution: | Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, USA. |
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| Abstract: | A one-pot synthesis of allenes by the 2-nitrobenzenesulfonylhydrazide-mediated coupling of hydroxyaldehydes or ketones with alkynyl trifluoroborate salts is reported. This mild process involves in situ formation of a sulfonylhydrazone that reacts with alkynyl trifluoroborates to generate a transient propargylic hydrazide species. Decomposition of this unstable hydrazide via an intermediate monoalkyldiazine produces the allene products through an alkene walk mechanism. |
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