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Intermolecular Metal‐Free Cyclopropanation of Alkenes Using Tosylhydrazones
Author(s) -
Barluenga José,
Quiñones Noelia,
TomásGamasa María,
Cabal MaríaPaz
Publication year - 2012
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.201200149
Subject(s) - cyclopropanation , chemistry , diazo , alkene , styrene , intermolecular force , organic chemistry , molecule , catalysis , copolymer , polymer
We describe the first general method for the metal‐free cyclopropanation of alkenes by using N ‐tosylhydrazones as an in situ source of diazo compounds. This new method works with a wide variety of alkenes (styrene derivatives, dienes, enynes, and electron‐deficient alkenes) by using N ‐tosylhydrazones derived from various ketones or aldehydes (aromatic, aliphatic, enones). The reaction is performed with the use of K 2 CO 3 as a base to form the diazo species and is compatible with a wide array of functional groups.