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Gold‐Catalyzed Synthesis of 1‐Naphthylcarbenoids and Their Synthetic Utilization in Cyclopropanation Reactions
Author(s) -
Lauterbach Tobias,
Ganschow Michael,
Hussong Matthias W.,
Rudolph Matthias,
Rominger Frank,
Hashmi A. Stephen K.
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201400104
Subject(s) - cyclopropanation , intermolecular force , intramolecular force , chemistry , carbene , catalysis , combinatorial chemistry , coupling reaction , nanotechnology , organic chemistry , molecule , materials science
1‐Naphthylcarbenoids are generated via 1,2‐acyl migration and subsequent carbene shift from simple, easily available diyne starting materials. These highly reactive species were allowed to react with differently substituted alkenes in both intermolecular and intramolecular fashions. In the intermolecular cases even a simple 1:1 ratio of the starting materials delivered the corresponding cyclopropylnaphthalenes in high yields by the use of a gold(III) catalyst. The methodology offers a completely new approach to these valuable targets, the new route represents an efficient alternative to common methods that are based on cross‐coupling strategies.