Synthetic applications of gold-catalyzed ring expansions
نویسندگان
چکیده
The development of new methodologies catalyzed by late transition metals involving cycloisomerizations of strained rings can open new venues for the synthesis of structurally complex molecules with interesting biological activities. Herein we summarize, from both a synthetic as well as a mechanistic point of view, the most recent developments in gold-catalyzed ring expansions.
منابع مشابه
Gold(I)-catalyzed ring expansions of unactivated alkynylcyclopropanes to (e)-2-alkylidenecyclobutanamines in the presence of sulfonamides.
The ring expansion of cyclopropane derivatives provides a powerful method to construct synthetically useful four-membered carbocycles. Herein, a new type of gold(I)-catalyzed ring expansion of an unactivated alkynylcyclopropane/sulfonamide trapping strategy to (E)-2-alkylidenecyclobutanamines was described. The reaction tolerates a range of aryl and alkyl substituents with moderate to good yields.
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The rearrangement of 1-alkynyl cyclobutanols and cyclopropanols to alkylidene cycloalkanones catalyzed by cationic triarylphosphine gold(I) complexes is described. The reaction tolerates terminal alkynes as well as alkyl, aryl, and halo-substitution at the acetylenic position and stereoselectively provides a single olefin isomer. The gold(I)-catalyzed rearrangement is stereospecific with regard...
متن کاملStrained small rings in gold-catalyzed rapid chemical transformations.
Gold-catalyzed reactions, which have been widely explored over the past several years, are powerful tools in organic synthesis to access complex molecular frameworks, and some corresponding excellent reviews have been reported. However, little attention has been paid to summarize the reactions of strained small-ring-containing molecules catalyzed by gold. This critical review mainly puts its em...
متن کاملGold-catalyzed propargylic substitutions: Scope and synthetic developments
This personal account summarizes our recent developments in gold-catalyzed direct substitutions on propargylic (allylic, benzylic) alcohols, with various nucleophiles (and bi-nucleophiles) based on the σ- and/or π-acidity of gold(III) complexes. Synthetic developments are also briefly described.
متن کاملAccess to polysubstituted indoles or benzothiophenes via palladium-catalyzed cross-coupling of furfural tosylhydrazones with 2-iodoanilines or 2-iodothiophenols.
Palladium-catalyzed cross-coupling of furfural tosylhydrazones with 2-iodoanilines or 2-iodothiophenols produces polysubstituted indoles or benzothiophenes, respectively. The reaction proceeds through 2-furylmethylene palladium iodide intermediates, which undergo furan ring opening followed by ring closure to form indoles or benzothiophenes. This reaction will expand the synthetic applications ...
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عنوان ژورنال:
دوره 7 شماره
صفحات -
تاریخ انتشار 2011