Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, USA.
J Am Chem Soc. 2012 Apr 4;134(13):5782-5. doi: 10.1021/ja301489n. Epub 2012 Mar 27.
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.
本文报道了通过 2-硝基苯磺酰肼介导的羟醛或酮与炔基三氟硼酸盐盐的偶联反应一锅法合成烯丙基的方法。该温和的过程涉及磺酰腙的原位形成，该磺酰腙与炔基三氟硼酸盐反应生成瞬态丙炔基酰肼物种。通过中间单烷基亚嗪分解这种不稳定的酰肼，通过烯烃行走机制产生烯丙基产物。
